GB741014A - Steroid compounds - Google Patents
Steroid compoundsInfo
- Publication number
- GB741014A GB741014A GB19382/53A GB1938253A GB741014A GB 741014 A GB741014 A GB 741014A GB 19382/53 A GB19382/53 A GB 19382/53A GB 1938253 A GB1938253 A GB 1938253A GB 741014 A GB741014 A GB 741014A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trione
- hydroxy
- hydroxypregnane
- dione
- trihydroxypregnan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises an 11a ,17a -dihydroxypregnane - 3,20 - dione and an 11a -acyloxy derivative thereof wherein the acyl radical contains up to eight carbon atoms, and the preparation thereof by contacting a saturated secondary hydroxy-steroid containing no primary hydroxy group with an organic hypochlorite, e.g. t-butyl hypochlorite, under substantially anhydrous conditions to convert the secondary hydroxy group to a keto group. The reaction may be effected in the presence of an organic solvent, e.g. t-butyl alcohol, t-amyl alcohol, chloroform, ethylene dichloride, pentane or hexane at a temperature between about -20 DEG and 50 DEG C. As starting materials there may be used steroids having the formula: <FORM:0741014/IV(a)/1> wherein R1 represents H, a -hydroxy or an acyloxy ester; R2 is H or hydroxy; and R3 is acetyl or acyloxyacetyl. Examples disclose the production of pregnane-3,11,20-trione, 17a -hydroxy - 21 - acetoxypregnane - 3,11,20-trione, 17a - hydroxypregnane - 3,11,20-trione, cholestan - 3 - one, allopregnane-3-11-20 - trione, 17a - hydroxy - 21 - bromopregnane - 3,11,20 - trione, 11a - hydroxypregnane - 3,20 - dione, 21 - chloro - 17a -hydroxypregnane - 3,11,20 - trione, 11a ,17a -dihydroxypregnane - 3,20 - dione, 11a - acetoxy-17a - hydroxypregnane - 3,20 - dione, 11a , 21 - diacetoxy - 17a - hydroxypregnane - 3,20-dione. Specifications 738,611, 739,175 and 740,987 are referred to. 21 - Bromo - 3a or b , 11a or b , 17a - trihydroxypregnan - 20 - one is obtained by treating 3a or b , 11a or b , 17a -trihydroxypregnan-20-one with bromine in chloroform. 21-Acetoxy-3a or b , 11a or b , 17a -trihydroxypregnan-20-one is obtained by heating 21-bromo-3a or b , 11a or b , 17a -trihydroxy-pregnan - 20 - one with anhydrous potassium acetate in the presence of a trace of potassium iodide. 11a ,21 - Diacetoxy - 3a ,17a - dihydroxypregnan-20-one is obtained from 21-bromo-11a - acetoxy - 3a ,17a - dihydroxypregnan-20-one.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US741014XA | 1952-07-16 | 1952-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB741014A true GB741014A (en) | 1955-11-23 |
Family
ID=22117738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19382/53A Expired GB741014A (en) | 1952-07-16 | 1953-07-13 | Steroid compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB741014A (en) |
-
1953
- 1953-07-13 GB GB19382/53A patent/GB741014A/en not_active Expired
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