GB753239A - Improvements in or relating to the preparation of steroid substances - Google Patents
Improvements in or relating to the preparation of steroid substancesInfo
- Publication number
- GB753239A GB753239A GB3273053A GB3273053A GB753239A GB 753239 A GB753239 A GB 753239A GB 3273053 A GB3273053 A GB 3273053A GB 3273053 A GB3273053 A GB 3273053A GB 753239 A GB753239 A GB 753239A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- liquid ammonia
- oxotigogenin
- spirostane
- oxo
- 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
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- 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
3-Hydroxy-11-ketosteroids and esters thereof are prepared by reduction of the corresponding diesterified 3,12-dihydroxy-11-ketosteroids with an alkali or alkaline-earth metal in the presence of liquid ammonia. The preferred compounds have the general formula <FORM:0753239/IV(a)/1> where X and Y each represent hydrogen or a monovalent substituent, and R is a hydroxy or esterified hydroxy group in the a or b configuration, and the starting materials should preferably be free from substituents (e.g. free hydroxy groups) which can act as a source of protons in liquid ammonia. Specified metals which may be used are lithium, sodium, potassium, calcium, strontium and barium; and the reaction may be effected in an organic solvent, e.g. ether, toluene or tetrahydrofuran, preferably at a temperature between - 60 DEG C. and - 33 DEG C. Specified esterifying groups in the starting materials are acetyl, propionyl, benzoyl and mesyl. In examples (I) 3b ,12b -diacetoxy-11-oxo-5a ,22a -spirostane in ether-dioxan is added to a solution of lithium in liquid ammonia, the product decomposed with ammonium chloride, and the residue after evaporation of ammonia treated with aqueous-ethanolic potassium hydroxide to yield 3b -hydroxy-11-oxo - 5a ,22a - spirostane; (2) as in (1) using sodium, potassium, calcium or barium as the active metal; the reaction complex is also decomposed with bromobenzene or ethylene dichloride when the alkaline earths are employed. The resultant spirostane is further esterified to 11-oxotigogenin benzoate, or the saponification step replaced by acetylation with acetic-anhydride-pyridine to yield 11-oxotigogenin acetate; (3) 11-oxotigogenin and its benzoate are also prepared from 3b -acetoxy-12b -mesyloxy-and 3b ,12b - dibenzoyloxy - 11 - oxo - 5a ,22a -spirostanes; (4) ethereal methyl 3a ,12b -diacetoxy-11-oxocholanate is added to calcium in liquid ammonia, excess metal destroyed with bromobenzene and after evaporation and saponification of the residue, 3a -hydroxy-11-oxocholanic acid is isolated with HCl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3273053A GB753239A (en) | 1953-11-25 | 1953-11-25 | Improvements in or relating to the preparation of steroid substances |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3273053A GB753239A (en) | 1953-11-25 | 1953-11-25 | Improvements in or relating to the preparation of steroid substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB753239A true GB753239A (en) | 1956-07-18 |
Family
ID=10343159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3273053A Expired GB753239A (en) | 1953-11-25 | 1953-11-25 | Improvements in or relating to the preparation of steroid substances |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB753239A (en) |
-
1953
- 1953-11-25 GB GB3273053A patent/GB753239A/en not_active Expired
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