GB773926A - Improvements relating to pregnane compounds - Google Patents
Improvements relating to pregnane compoundsInfo
- Publication number
- GB773926A GB773926A GB23030/55A GB2303055A GB773926A GB 773926 A GB773926 A GB 773926A GB 23030/55 A GB23030/55 A GB 23030/55A GB 2303055 A GB2303055 A GB 2303055A GB 773926 A GB773926 A GB 773926A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ketal
- pregnane
- dione
- tetrol
- bis
- 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 pregnane-5a ,11b ,-17a ,21-tetrol-3,20-dione and the 21-acetate thereof, and the 3,20-bisethylene ketal derivatives of both compounds, and a process for producing pregnane compounds by reducing D 5 - pregnene - 11b ,17a ,21 - triol - 3,20 - dione - 5a ,6a - oxide 21-lower fatty acid ester 3,20-bis-lower alkylene ketal in an inert organic solvent, e.g. tetrahydrofuran, with lithium aluminium hydride to form a pregnane-5a ,11b ,17a ,21-tetrol -3,20 - dione 3,20 - bis - lower alkylene ketal, and, if desired, hydrolysing with acid said ketal to produce pregnane-5a ,11b ,17b ,21-tetrol-3,20-dione. The above process may be modified in that the D 5-pregnene-11b ,17a ,21-triol-3,20-bis -lower alkylene ketal is prepared from a bis-lower alkylene ketal of a hydrocortisone lower fatty acid ester by reaction with an organic per-acid. The lower fatty acid acyl radicals and the lower alkylene ketal radicals contain 1 to 4 carbon atoms, suitable acyl radicals being acetyl, propionyl and butyryl radicals and suitable alkelene radicals being ethylene ketal, propylene ketal and methylpropylene radicals. The reaction with the organic peracid may be carried out with perbenzoic or monoperphthalic acid at room temperature in an inert organic solvent such as chloroform, carbon tetrachloride or ethyl acetate, to form a mixture of the 5a ,6a -oxide and 5b ,6b -oxide which may be resolved by chromatography or used as a mixture for the following reduction step with lithium aluminium hydride. In the examples pregnane-11b ,17a ,21-triol - 3,20 - dione - 5a ,6a - oxide 21 - acetate-3,20-bisethylene ketal and the corresponding 5b ,6b -oxide are prepared. The mixture of oxides or the 5a ,6a -oxide are reduced with lithium aluminium hydride to form pregnane-5a ,11b ,17a ,21 - tetrol - 3,20 - dione 3,20 - bis-ethylene ketal which is acetylated to form the corresponding 21-acetate, or treated with sulphuric acid to form pregnane-5a ,11b ,17a ,21-tetrol-3,20-dione which is acetylated to form the corresponding 21-acetate. The pregnane-5a ,-11b ,17a ,21 - tetrol - 3,20 - dione 3,20 - bis-ethylene ketal 21-acetate is also saponified with alcoholic potassium hydroxide to form the corresponding 21-hydroxy compound.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US773926XA | 1954-08-16 | 1954-08-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB773926A true GB773926A (en) | 1957-05-01 |
Family
ID=22137785
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23030/55A Expired GB773926A (en) | 1954-08-16 | 1955-08-10 | Improvements relating to pregnane compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB773926A (en) |
-
1955
- 1955-08-10 GB GB23030/55A patent/GB773926A/en not_active Expired
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