CN110437294A - A method of preparing Trenbolone acetate - Google Patents
A method of preparing Trenbolone acetate Download PDFInfo
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- CN110437294A CN110437294A CN201910658198.5A CN201910658198A CN110437294A CN 110437294 A CN110437294 A CN 110437294A CN 201910658198 A CN201910658198 A CN 201910658198A CN 110437294 A CN110437294 A CN 110437294A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
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Abstract
The invention discloses a kind of methods for preparing Trenbolone acetate, belong to the processing technology of preparing field of hormone medicine.This method is with 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- ketone is starting material, is alcohol by 17 ketone of reduction, hydrolyzes 3 ketals, Trenbolone acetate is prepared in oxidative dehydrogenation and 17 alcohol acetylations.Trenbolone acetate synthesis route of the present invention, raw material is cheap and easy to get, and reaction controlling simplicity by-product is few, purifying is easy, and gross production rate is high, there is high competitiveness on production cost and operability, it is suitble to industrialization large-scale production, it is with good economic efficiency.
Description
Technical field
The present invention relates to the processing technology of preparing field of hormone medicine, and in particular to a kind of Trenbolone acetate for preparing
Method.
Background technique
Trenbolone acetate (Trenbolone Acetate), the entitled 17 β-acetoxyl group-female steroid -4,9 of chemistry, 11- tri-
Alkene -3- ketone is a kind of preferable protein anabolic hormone of effect, can remarkably promote beef cattle growth, while can also significantly reduce meat
Expect ratio, improve meat, has obtained mass production in foreign countries as beef cattle growing agent and be widely used, especially had very in North America
Big market.Since it also has prevention effect to rabid ox disease, this increases the demand of Trenbolone acetate constantly.
The synthetic route of existing Trenbolone acetate is longer, some reaction yields are extremely low, makes obtaining for final products crystallization
It obtains very difficult.Zhang Huyue etc. (Fudan Journal (medicine) 2002,29 (3): 211-212) reports a kind of Trenbolone acetate
Preparation method, with female steroid -4,9- diene -3,17- diketone be starting material, p-methyl benzenesulfonic acid is catalyst, to 3- carbonyls
It is protected, is taking reduction, hydrolysis, dehydrogenation obtains Trenbolone；Last Trenbolone and acetic anhydride carry out esterification, obtain group
Vigorous dragon acetate, specific route are as follows:
The route steps are longer, and by-product is more, are unable to get solid product, matter if any two-step reaction step 2) and step 3
Measure low, yield is low, needs to use highly toxic solvent benzol, is unfavorable for industrialized production.
Route disclosed in Chinese patent CN102399253 (the rich biology of section's benefit) is with 17 beta-hydroxies-female steroid -4,9- diene -3-
Ketone is raw material, and by diacetyl, enol ester hydrolysis and oxidative dehydrogenation obtain Trenbolone acetate, and specific route is as follows:
The route carries out 17 hydroxy esterifications first, limits Trenbolone by other Esterification possibility, selective hydrolysis
Enol ester control is more difficult, is easy to happen hydrolysis and not exclusively or excessively hydrolyzes, leads to purification difficult, it is difficult to be mass produced.
Route disclosed in Chinese patent CN102924553 (common medicine company) is to report above-mentioned Zhang Huyue etc. in route
Acidic catalyst is changed to chloroacetic chloride/methanol by p-methyl benzenesulfonic acid, which uses a large amount of acid reagent chloroacetic chlorides, and corrosivity is right greatly
Production equipment requires height, and environmental pollution is serious, and the big processing of wastewater flow rate is difficult, and gross production rate, which has no, to be significantly improved.
Route disclosed in Chinese patent CN108017682 (monarch's industry medicine company), for raw material, passes through potassium boron hydrogen with 4,9 ring-opening products
Reduction, acid catalyzed condensation cyclization, oxidative dehydrogenation and esterification obtain Trenbolone acetate, and specific route is as follows:
The control of potassium boron hydrogen reduction poor selectivity is difficult in the route, and acid catalyzed condensation cyclization yield is not high, and purifying difficulty is big,
These all limit the extensive industrialization of this route.
Summary of the invention
The purpose of the present invention is to solve the above problems present in existing Trenbolone acetate preparation process, provide
A kind of method of new efficient preparation Trenbolone acetate
The purpose of the present invention is what is realized in the following way:
The present invention provides a kind of method for preparing Trenbolone acetate, the synthetic route of this method is as follows:
3- ethylenedioxy female steroid-Δ 5,10, Δ 9,11- diene -17- ketone
Trenbolone acetate
Specifically comprise the following steps:
1) 17 ketone reduction reaction steps: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- ketone (1), which is dissolved in, to be had
Solvent is added reducing agent and is stirred to react at 0~60 DEG C, after thin-layer chromatographic analysis shows raw material fully reacting, be cooled to-
5~10 DEG C, elutriation filters to obtain 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- alcohol (2)；
2) 3 hydrolysis of ketal reaction steps: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- alcohol (2) is added to
In solvent, acid solution is added, 20~80 DEG C of temperature is controlled, is stirred to react, after fully reacting, elutriation is extracted with dichloromethane,
It is washed to neutrality, obtains female steroid-Δ5,10, Δ9,11The dichloromethane solution of diene -17- alcohol -3- ketone (3)；
3) oxidative dehydrogenation step: female steroid-Δ5,10, Δ9,11The dichloromethane solution of diene -17- alcohol -3- ketone (3) adds
Oxidising agent controls reaction temperature at 0~40 DEG C, is stirred to react, filters after fully reacting, collects filtrate, be washed to neutrality, dense
Solid is precipitated in contracting solvent, obtains female steroid -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4)；
4) 17 alcohol acetylization reaction steps: -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) of female steroid is dissolved in organic
Catalyst and aceticanhydride is added in solvent, controls temperature under -5~50 DEG C of ranges, is stirred to react, and after the reaction was completed, is concentrated, cooling
To -10~10 DEG C of filterings, Trenbolone acetate is obtained.
Further, organic solvent described in step 1 refer to methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, in the tert-butyl alcohol
One kind, volumetric usage be substrate 3- ethylenedioxy female steroid-Δ5,10, Δ9,111~10 times of diene -17- ketone (1) weight
Amount；The reducing agent is one of potassium boron hydrogen, sodium borohydride, and weight consumption is substrate 3- ethylenedioxy female steroid-
Δ5,10, Δ9,110.05~5 times of diene -17- ketone (1) weight.
Further, solvent described in step 2 is water, acetone, butanone, tetrahydrofuran, one of methylene chloride or several
Kind, volumetric usage is substrate 3- ethylenedioxy female steroid-Δ5,10, Δ9,110.1~10 times of diene -17- alcohol (2) weight；
The acid solution is one of acetic acid, sulfuric acid, hydrochloric acid, oxalic acid, formic acid, phosphate aqueous solution, wherein acetic acid, oxalic acid, formic acid
Volumetric concentration be 30~80%, sulfuric acid, hydrochloric acid, phosphoric acid volumetric concentration be 3~15%, the acid solution volumetric usage be substrate
3- ethylenedioxy female steroid-Δ5,10, Δ9,111~10 times of diene -17- alcohol (2) weight；The volumetric usage of the methylene chloride
For substrate 3- ethylenedioxy female steroid-Δ5,10, Δ9,115~20 times of diene -17- alcohol (2) weight.
Further, oxidising agent described in step 3 is one of tetrachloroquinone, chloro- 5, the 6- dicyanoquinone of 2,3- bis-
Or composition, weight consumption are substrate 3- ethylenedioxy female steroid-Δ5,10, Δ9,11The 0.1 of diene -17- alcohol (2) weight~
5 times.
Further, organic solvent described in step 4 is one of methylene chloride, dichloroethanes, acetone, butanone, toluene
Or it is several, volumetric usage be substrate female steroid -4,9,1~10 times of 11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) weight；Institute
The catalyst stated is p-methyl benzenesulfonic acid or 4- (dimethylamino) pyridine, and weight consumption is substrate female steroid -4,9,11 triolefin -17-
0.01~2 times of amount of alcohol -3- ketone (Trenbolone) (4) weight；The volumetric usage of the aceticanhydride is -4,9,11 triolefin of substrate female steroid -
0.5~5 times of 17- alcohol -3- ketone (Trenbolone) (4) weight.
Further, when the acid solution described in the step 2 is one of acetic acid, oxalic acid or aqueous formic acid, described is molten
There is no need to individually additions again for agent.
Involved raw material can sufficiently be obtained by commercially available mode in the method for the present invention.
Compared with the prior art, the invention has the advantages that:
1, the preparation method of Trenbolone acetate of the present invention, raw material is cheap and easy to get, and raw material 3- ethylenedioxy is female
Steroid-Δ5,10, Δ9,11Diene -17- ketone is cheap, and market supply is stablized, and agents useful for same is that common pharmacy industry is former in route
Material；
2, the involved reaction of the method for the present invention is not susceptible to overreaction and incomplete reaction, and reaction controlling is easy, by-product
Object is few；
3, the method for the present invention purifying is easy, and gross mass yield is higher than 60%, and purity is up to 99% or more；
4, the method for the present invention has high competitiveness on production cost and operability, is suitble to industrialization extensive raw
It produces, it is with good economic efficiency.
Specific embodiment
The present invention is further elaborated below with reference to embodiment, is not intended to restrict the invention.
Specific experiment step or condition person are not specified in embodiment, according to conventional described in disclosure in the art
The operation of experimental method can carry out, and manufacturer person is not specified in agents useful for same or equipment, and being can be by the routine of commercially available acquisition
Product.
1 reduction reaction of example: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11The preparation 1 of diene -17- alcohol
10 grams of 3- ethylenedioxy female steroid-Δs are added in reaction flask5,10, Δ9,11Diene -17- ketone (1), 80 milliliters of isopropyls
Alcohol, 5 grams of sodium borohydrides, are heated to 60 DEG C and are stirred to react, and after the reaction was completed, are cooled to 10 DEG C, solid is precipitated in elutriation, filtering, dries
It is dry, obtain 9.2 grams of 3- ethylenedioxy female steroid-Δs5,10, Δ9,11Diene -17- alcohol (2).
2 reduction reaction of example: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11The preparation 2 of diene -17- alcohol
10 grams of 3- ethylenedioxy female steroid-Δs are added in reaction flask5,10, Δ9,11Diene -17- ketone (1), 100 milliliters of second
Alcohol, 10 grams of potassium borohydrides, 0 DEG C of temperature of control are stirred to react, and after the reaction was completed, are cooled to -5 DEG C, and solid is precipitated in elutriation, filtering,
Drying, obtains 9.1 grams of 3- ethylenedioxy female steroid-Δs5,10, Δ9,11Diene -17- alcohol (2).
3 reduction reaction of example: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11The preparation 3 of diene -17- alcohol
10 grams of 3- ethylenedioxy female steroid-Δs are added in reaction flask5,10, Δ9,11Diene -17- ketone (1), 80 ml methanols,
5 grams of potassium borohydrides are heated to 40 DEG C and are stirred to react, and after the reaction was completed, are cooled to 6 DEG C, solid is precipitated in elutriation, filtering, and drying obtains
9.0 grams of 3- ethylenedioxy female steroid-Δs5,10, Δ9,11Diene -17- alcohol (2).
4 reduction reaction of example: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11The preparation 4 of diene -17- alcohol
10 grams of 3- ethylenedioxy female steroid-Δs are added in reaction flask5,10, Δ9,11Diene -17- ketone (1), 80 milliliters of positive fourths
Alcohol, 30 grams of potassium borohydrides, are heated to 30 DEG C and are stirred to react, and after the reaction was completed, are cooled to 5 DEG C, solid is precipitated in elutriation, filtering, dries
It is dry, obtain 9.3 grams of 3- ethylenedioxy female steroid-Δs 5,10, Δ 9,11- diene -17- alcohol (2).
The preparation 1 of -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) of 5 female steroid of example
9.0 grams of 3- ethylenedioxy female steroid-Δs are added in reaction flask5,10, Δ9,11Diene -17- alcohol (2), 60 milliliters of tetrahydros
The aqueous hydrochloric acid solution of furans, 9 milliliter of 15% volumetric concentration, 20 DEG C of temperature of control are stirred to react to complete, elutriation, and 100 millis are added
Methylene chloride extraction is risen, organic phase is washed to neutrality, obtains female steroid-Δ5,10, Δ9,11The dichloro of diene -17- alcohol -3- ketone (3)
Dichloromethane.In dichloromethane solution be added 40 grams of chloro- 5,6- dicyanoquinones of 3- bis-, control 20 DEG C of temperature, be stirred to react to
Completely, filtering reacting liquid collects filtrate, and concentration is collected by filtration the solid of precipitation, obtains 6.5 grams of female steroids -4,9 after cooling, and 11 3
Alkene -17- alcohol -3- ketone (Trenbolone) (4).
The preparation 2 of -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) of 6 female steroid of example
9.0 grams of 3- ethylenedioxy female steroid-Δs are put into reaction flask5,10, Δ9,11Diene -17- alcohol (2), 60 milliliter third
The aqueous sulfuric acid of ketone, 10 milliliter of 8% volumetric concentration, 20 DEG C of temperature of control are stirred to react to complete, elutriation, are added 130 milliliters
Methylene chloride extraction, organic phase are washed to neutrality, obtain female steroid-Δ5,10, Δ9,11The dichloromethane of diene -17- alcohol -3- ketone (3)
Alkane solution.15 grams of tetrachloroquinones and 10 grams of chloro- 5,6- dicyanoquinones of 2,3- bis- are added in dichloromethane solution, control temperature 40
DEG C, it is stirred to react to complete, filtering reacting liquid, collects filtrate, concentration is collected by filtration the solid of precipitation, obtains 6.8 grams after cooling
- 4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) of female steroid.
The preparation 3 of -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) of 7 female steroid of example
9.0 grams of 3- ethylenedioxy female steroid-Δs are put into reaction flask5,10, Δ9,11Diene -17- alcohol (2), 40 milliliter 50%
The aqueous acetic acid of volumetric concentration is heated to 80 DEG C and is stirred to react to complete, elutriation, is extracted with 160 milliliters of methylene chloride, washing
Organic phase obtains female steroid-Δ to neutrality5,10, Δ9,11The dichloromethane solution of diene -17- alcohol -3- ketone (3).Methylene chloride is molten
15 grams of chloro- 5,6- dicyanoquinones of 2,3- bis- are added in liquid, control 0 DEG C of temperature, is stirred to react to complete, filtering reacting liquid, receives
Collect filtrate, concentration is collected by filtration the solid of precipitation, obtains 6.4 grams of female steroids -4,9, (group is vigorous for 11 triolefin -17- alcohol -3- ketone after cooling
Dragon) (4).
The preparation 4 of -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) of 8 female steroid of example
9.0 grams of 3- ethylenedioxy female steroid-Δs are put into reaction flask5,10, Δ9,11Diene -17- alcohol (2), 60 milliliters of dichloros
The phosphate aqueous solution of methane, 10 milliliter of 8% volumetric concentration is heated to 30 DEG C and is stirred to react to complete, washing organic phase to neutrality,
Obtain female steroid-Δ 5,10, Δ 9, the dichloromethane solution of 11- diene -17- alcohol -3- ketone (3).10 are added in dichloromethane solution
Gram tetrachloroquinone controls 30 DEG C of temperature, is stirred to react to complete, filtering reacting liquid, collects filtrate, and concentration is filtered after cooling and received
Collect the solid being precipitated, obtains 6.3 grams of female steroids -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4).
The preparation 1 of 9 Trenbolone acetate of example
6.0 grams of female steroids -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) and 28 milliliters of acetone are added in reaction flask, add
Enter 0.2 gram of 4-dimethylaminopyridine and 6.5 milliliters of aceticanhydrides, control 30 DEG C of temperature, is stirred to react to complete, concentration removes organic molten
Agent is cooled to 0 DEG C, and the solid of precipitation is collected by filtration, drying, obtains 5.6 grams of Trenbolone acetates, and gained Trenbolone acetate is molten
73.5~75.3 DEG C of point, HPLC content 99.3%, gross mass yield 61.3%.
The preparation 2 of 10 Trenbolone acetate of example
6.0 grams of -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) of female steroid and 28 milliliters of dichloromethanes are added in reaction flask
0.1 gram of 4-dimethylaminopyridine and 7.4 milliliters of aceticanhydrides is added in alkane, controls 20 DEG C of temperature, is stirred to react to complete, concentration removing
Organic solvent is cooled to 5 DEG C, and the solid of precipitation is collected by filtration, and drying obtains 6.0 grams of Trenbolone acetates.Gained Trenbolone vinegar
73.0~75.1 DEG C of acid esters fusing point, HPLC content 99.0%, gross mass yield 66.6%.
The preparation 3 of 11 Trenbolone acetate of example
6.0 grams of female steroids -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) and 28 milliliters of toluene are added in reaction flask, add
Enter 0.15 gram of p-methyl benzenesulfonic acid and 7.5 milliliters of aceticanhydrides, control temperature 50 C, is stirred to react to complete, concentration removing organic solvent,
- 5 DEG C are cooled to, the solid of precipitation is collected by filtration, is dried, 5.65 grams of Trenbolone acetates are obtained, gained Trenbolone acetate is molten
73.5~75.0 DEG C of point, HPLC content 99.4%, gross mass yield 62.0%.
The preparation 4 of 12 Trenbolone acetate of example
6.0 grams of -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) of female steroid and 28 milliliter of two chloroethene are added in reaction flask
Alkane, is added 0.15 gram of p-methyl benzenesulfonic acid and 7.5 milliliters of aceticanhydrides, controls -5 DEG C of temperature, is stirred to react to complete, concentration removes organic
Solvent is cooled to -10 DEG C, and the solid of precipitation is collected by filtration, and drying obtains 5.7 grams of Trenbolone acetates, gained Trenbolone acetic acid
74.0~75.5 DEG C of ester fusing point, HPLC content 99.2%, gross mass yield 64.1%.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
In the technical scope disclosed by the present invention, any changes or substitutions that can be easily thought of by anyone skilled in the art,
It should be covered by the protection scope of the present invention.
Claims (6)
1. a kind of method for preparing Trenbolone acetate, which is characterized in that the synthetic route of this method is as follows:
Specifically comprise the following steps:
1) 17 ketone reduction reaction steps: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- ketone (1) is dissolved in organic molten
Agent is added reducing agent and is stirred to react at 0~60 DEG C, after thin-layer chromatographic analysis shows raw material fully reacting, it is cooled to -5~
10 DEG C, elutriation filters to obtain 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- alcohol (2)；
2) 3 hydrolysis of ketal reaction steps: 3- ethylenedioxy female steroid-Δ5,10, Δ9,11Diene -17- alcohol (2) is added to solvent
In, acid solution is added, 20~80 DEG C of temperature is controlled, is stirred to react, after fully reacting, elutriation is extracted with dichloromethane, washing
To neutrality, female steroid-Δ is obtained5,10, Δ9,11The dichloromethane solution of diene -17- alcohol -3- ketone (3)；
3) oxidative dehydrogenation step: female steroid-Δ5,10, Δ9,11The dichloromethane solution oxygenation of diene -17- alcohol -3- ketone (3)
Reagent controls reaction temperature at 0~40 DEG C, is stirred to react, filters after fully reacting, collect filtrate, be washed to neutrality, is concentrated molten
Solid is precipitated in agent, obtains female steroid -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4)；
4) 17 alcohol acetylization reaction steps: female steroid -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) are dissolved in organic solvent,
Catalyst and aceticanhydride is added, controls temperature under -5~50 DEG C of ranges, is stirred to react, after the reaction was completed, concentration is cooled to -10
~10 DEG C of filterings, obtain Trenbolone acetate.
2. preparation Trenbolone acetate method according to claim 1, which is characterized in that organic solvent described in step 1
Refer to one of methanol, ethyl alcohol, normal propyl alcohol, isopropanol, n-butanol, tert-butyl alcohol, volumetric usage is the Asia substrate 3- second dioxy
Base female steroid-Δ5,10, Δ9,111~10 times of amount of diene -17- ketone (1) weight；The reducing agent is potassium boron hydrogen, in sodium borohydride
One kind, weight consumption be substrate 3- ethylenedioxy female steroid-Δ5,10, Δ9,11The 0.05~5 of diene -17- ketone (1) weight
Times.
3. preparation Trenbolone acetate method according to claim 1, which is characterized in that solvent described in step 2 is
Water, acetone, butanone, tetrahydrofuran, one or more of methylene chloride, volumetric usage are that substrate 3- ethylenedioxy is female
Steroid-Δ5,10, Δ9,110.1~10 times of diene -17- alcohol (2) weight；The acid solution is acetic acid, sulfuric acid, hydrochloric acid, oxalic acid, first
Acid, one or more of phosphate aqueous solution, wherein acetic acid, oxalic acid, formic acid volumetric concentration be 30~80%, sulfuric acid, hydrochloric acid,
The volumetric concentration of phosphoric acid is 3~15%, and the acid solution volumetric usage is substrate 3- ethylenedioxy female steroid-Δ5,10, Δ9,11-
1~10 times of diene -17- alcohol (2) weight；The volumetric usage of the methylene chloride is substrate 3- ethylenedioxy female steroid-
Δ5,10, Δ9,115~20 times of diene -17- alcohol (2) weight.
4. preparation Trenbolone acetate method according to claim 1, which is characterized in that oxidising agent described in step 3
For one of tetrachloroquinone, chloro- 5, the 6- dicyanoquinone of 2,3- bis- or composition, weight consumption is the Asia substrate 3- second dioxy
Base female steroid-Δ 5,10, Δ 9,0.1~5 times of 11- diene -17- alcohol (2) weight.
5. preparation Trenbolone acetate method according to claim 1, which is characterized in that organic solvent described in step 4
For one or more of methylene chloride, dichloroethanes, acetone, butanone, toluene, volumetric usage is substrate female steroid -4,9,11
1~10 times of triolefin -17- alcohol -3- ketone (Trenbolone) (4) weight；The catalyst is p-methyl benzenesulfonic acid or 4- (diformazan ammonia
Base) pyridine, weight consumption be substrate female steroid -4,9,0.01~2 times of 11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) weight
Amount；The volumetric usage of the aceticanhydride is the 0.5~5 of substrate female steroid -4,9,11 triolefin -17- alcohol -3- ketone (Trenbolone) (4) weight
Times.
6. preparation Trenbolone acetate method according to claim 1, which is characterized in that the acid solution described in the step 2
When for one of acetic acid, oxalic acid or aqueous formic acid, there is no need to individually additions again for the solvent.
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| CN201910658198.5A CN110437294A (en) | 2019-07-21 | 2019-07-21 | A method of preparing Trenbolone acetate |
| PCT/CN2020/076924 WO2021012673A1 (en) | 2019-07-21 | 2020-02-27 | Method for preparing trenbolone acetate |
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| CN201910658198.5A CN110437294A (en) | 2019-07-21 | 2019-07-21 | A method of preparing Trenbolone acetate |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111848713A (en) * | 2020-06-26 | 2020-10-30 | 浙江神洲药业有限公司 | Preparation method of alkyl acid testosterone |
| CN111875655A (en) * | 2020-06-19 | 2020-11-03 | 浙江神洲药业有限公司 | Preparation method of testosterone propionate |
| WO2021012673A1 (en) * | 2019-07-21 | 2021-01-28 | 浙江神洲药业有限公司 | Method for preparing trenbolone acetate |
| EP4000688A1 (en) | 2020-11-19 | 2022-05-25 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of trenbolone acetate having a definite particle size distribution |
| EP4001288A1 (en) | 2020-11-19 | 2022-05-25 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of trenbolone acetate having a definite particle size distribution and a irregular hexagon plates crystal habit |
| EP4001289A1 (en) | 2020-11-19 | 2022-05-25 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of trenbolone and/or trenbolone acetate |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021012673A1 (en) * | 2019-07-21 | 2021-01-28 | 浙江神洲药业有限公司 | Method for preparing trenbolone acetate |
| CN111875655A (en) * | 2020-06-19 | 2020-11-03 | 浙江神洲药业有限公司 | Preparation method of testosterone propionate |
| CN111875655B (en) * | 2020-06-19 | 2021-12-21 | 浙江神洲药业有限公司 | Preparation method of testosterone propionate |
| CN111848713A (en) * | 2020-06-26 | 2020-10-30 | 浙江神洲药业有限公司 | Preparation method of alkyl acid testosterone |
| EP4000688A1 (en) | 2020-11-19 | 2022-05-25 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of trenbolone acetate having a definite particle size distribution |
| EP4001288A1 (en) | 2020-11-19 | 2022-05-25 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of trenbolone acetate having a definite particle size distribution and a irregular hexagon plates crystal habit |
| EP4001289A1 (en) | 2020-11-19 | 2022-05-25 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of trenbolone and/or trenbolone acetate |
| WO2022106566A1 (en) | 2020-11-19 | 2022-05-27 | F.I.S. - Fabbrica Italiana Sintetici S.P.A. | Process for the preparation of trenbolone acetate having a definite particle size distribution and a irregular hexagon plates crystal habit |
| WO2022106574A1 (en) | 2020-11-19 | 2022-05-27 | F.I.S. - Fabbrica Italiana Sintetici S.P.A. | Improved process for the preparation of trenbolone and/or trenbolone acetate |
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| WO2021012673A1 (en) | 2021-01-28 |
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