GB845441A - Process for the ethinylation of 17-keto-steroids - Google Patents
Process for the ethinylation of 17-keto-steroidsInfo
- Publication number
- GB845441A GB845441A GB7820/57A GB782057A GB845441A GB 845441 A GB845441 A GB 845441A GB 7820/57 A GB7820/57 A GB 7820/57A GB 782057 A GB782057 A GB 782057A GB 845441 A GB845441 A GB 845441A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethinyl
- prepared
- double bond
- androst
- dione
- 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
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
17-Hydroxy-17-ethinyl-steroids are prepared by reacting a 17-keto-steroid containing in the molecule a further unprotected keto group in the 3-position in continuous conjunction with at least one carbon-carbon double bond in the nucleus with an ethinylation reagent. Continuous conjugation excludes parallel conjugation such as exists when double bonds are present both in the 1, 2- and in the 4, 5-positions of the nucleus. The ethinylation may be carried out by means of acetylene and on alkali metal in liquid ammonia at a temperature below -40 DEG C. using more than 2 mols of alkali metal per mol of steroid, or by means of acetylene and an alkali metal achoholate of a tertiary alcohol-preferably more than 2 mols of alcoholate per mol of steroid. Suitable starting compounds are 3, 17-androstendiones and 19-nor-3, 17-androstendiones with at least one double bond in the 4, 5-or 1, 2 position and any other double bond in continuous conjugation. The starting compounds may contain further substituents, for example, in the 11-position, especially free or esterified hydroxy group. In the case where the unprotected 3-keto group is in continuous conjugation with a double bond in the 4(5)-position, the reaction may be carried out in the presence of acetone preferably in a quantity of more than 2 mols per mol of 17-ketosteroid reactant. In the examples 17-ethinyl-testosterone is prepared from androst-4-en-3, 17-dione, 19-nor-17-ethinyl-androst-4-en-17-ol-3-one is prepared from 19-nor-androst-4-en-3, 17-dione, and 17-ethinyl-D 6-dehydrotestosterone is prepared from D 4, 6-androstadien -3, 17-dione.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE845441X | 1956-03-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB845441A true GB845441A (en) | 1960-08-24 |
Family
ID=6774800
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7820/57A Expired GB845441A (en) | 1956-03-10 | 1957-03-08 | Process for the ethinylation of 17-keto-steroids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB845441A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4585591A (en) * | 1980-12-10 | 1986-04-29 | Mitsubishi Chemical Industries, Ltd. | 17β-ethynylsteroids and process for preparing same |
-
1957
- 1957-03-08 GB GB7820/57A patent/GB845441A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4585591A (en) * | 1980-12-10 | 1986-04-29 | Mitsubishi Chemical Industries, Ltd. | 17β-ethynylsteroids and process for preparing same |
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