GB940344A - Process for the manufacture of unsaturated steroids - Google Patents
Process for the manufacture of unsaturated steroidsInfo
- Publication number
- GB940344A GB940344A GB4439859D GB4439859D GB940344A GB 940344 A GB940344 A GB 940344A GB 4439859 D GB4439859 D GB 4439859D GB 4439859 D GB4439859 D GB 4439859D GB 940344 A GB940344 A GB 940344A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroids
- keto
- dibromides
- androstane
- bromo
- 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
- C07J75/00—Processes for the preparation of steroids in general
Abstract
940,344. 3-Keto-#<SP>4</SP>,<SP> 9(1</SP><SP>1)</SP>-and #<SP>1</SP>,<SP> 4</SP>,<SP> 9(11)</SP>- steroids. CIBA Ltd. Dec. 21, 1959 [Feb. 10, 1959; April 21, 1959], No. 43398/59. Heading C2U. 3-Keto- #<SP>4</SP>,<SP> 9(</SP><SP>11)</SP>-and 3-keto- #<SP>1</SP>,<SP> 4</SP>,<SP> 9(1</SP><SP>1)</SP>-steroids are prepared by brominating 11α-sulphonyloxy-3-keto-steroids saturated in ring A and heating the resulting 4-mono-bromo-ketones or 2,2-di-bromo-ketones (which are first converted by rearrangement with an acid into the corresponding 2,4-dibromides) with a lithium halide in a dialkyl-formamide, if desired in the presence of an alkali metal acylate or carbonate, and, when required de-brominating a 2-bromo- #<SP>4,9(11)</SP>- product so obtained by reduction. Bromination of 5 #-steroids with 1 mol of bromine yields 4- monobromides, while bromination of 5α-steroids with 2 mols of bromine yields 2,2- dibromides. If the 2,4-dibromides formed from the last-named are dehydrobrominated under relatively mild conditions e.g. below 120‹C. they yield #<SP>4</SP>, <SP>9</SP>(<SP>11</SP>)- dienes while the #<SP>1</SP>,<SP> 4</SP>,<SP> 9</SP>(<SP>11</SP>)-trienes are formed only if the temperature is raised. The starting material may belong to the cholestane, stigmastane, spirostane, cholane, etiochlolane, androstane or pregnane series, specific examples being 11α-sulphonyl esters of 11α, 17#-dihydroxy-5α and 5 #-androstan-3-ones and the 17α-methyl derivatives thereof; 11α-hydroxy-5α and 5#- androstane-3,17-diones; and 11α,17α-dihydroxy- 21-acyloxy-5α and 5 #-pregnane-3,20-diones and their 16-alkyl derivatives. Detailed examples are provided. 11α-Sulphonyloxy-3-keto-steroids saturated in ring A are prepared from the 11α-ols and reactive derivatives of sulphonic acids, especially of methane,- benzene- and p-toluene-sulphonic acids. 11α-Hydroxy-5α-androstane-3,17-dione is prepared by oxidation of the 3 #-ol. Specification 924,252 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6937059A CH385197A (en) | 1959-02-10 | 1959-02-10 | Process for the preparation of 4,9 (11) -and 1,4,9 (11) -3-keto-steroids |
| CH7233059 | 1959-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB940344A true GB940344A (en) | 1963-10-30 |
Family
ID=31716513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4439859D Expired GB940344A (en) | 1959-02-10 | 1959-12-21 | Process for the manufacture of unsaturated steroids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB940344A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190195338A1 (en) * | 2016-07-25 | 2019-06-27 | Bayerische Motoren Werke Aktiengesellschaft | Motorcycle Drive Device with Adjustable Backlash |
-
1959
- 1959-12-21 GB GB4439859D patent/GB940344A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190195338A1 (en) * | 2016-07-25 | 2019-06-27 | Bayerische Motoren Werke Aktiengesellschaft | Motorcycle Drive Device with Adjustable Backlash |
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