GB777995A - Allopregnan-3,6,11,20-tetrone and processes for its preparation - Google Patents
Allopregnan-3,6,11,20-tetrone and processes for its preparationInfo
- Publication number
- GB777995A GB777995A GB8821/55A GB882155A GB777995A GB 777995 A GB777995 A GB 777995A GB 8821/55 A GB8821/55 A GB 8821/55A GB 882155 A GB882155 A GB 882155A GB 777995 A GB777995 A GB 777995A
- Authority
- GB
- United Kingdom
- Prior art keywords
- progesterone
- allopregnan
- acetoxy
- aqueous
- methanolic
- 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 allopregnan-3,6,11, 20-tetrone and the preparation thereof by oxidizing allopregnan-11a -ol-3,6,20-trione with chromic acid, or by reducing 6,11-diketo-progesterone with zinc and acetic acid. The former process may be modified in that the allopregnan-11a -ol-3,6,20-trione is prepared by treating 6b ,11a -dihydroxy-progesterone with aqueous methanolic hydrochloric acid or potassium hydroxide; by epimerizing 6b ,11a -diacetoxy-progesterone with aqueous hydrogen chloride dissolved in chloroform containing about 1 per cent ethanol, saponifying the resulting 6a ,11a -diacetoxy-progesterone with two equivalents of methanolic potassium hydroxide at room temperature to form 6a ,11a -dihydroxy-progesterone which is then treated with aqueous methanolic hydrochloric acid; by brominating 11a -acetoxy-progesterone with N-bromosuccinimide, the resulting 6-bromo-11a -acetoxy-progesterone is treated with aqueous methanolic hydrochloric acid or aqueous methanolic silver nitrate to form allopregnan-11a -acetoxy-3,6,20-trione (this compound may also be obtained by reacting allopregnan-11a -ol-3,6,20-trione and acetic anhydride) which is then saponified with methanolic potassium hydroxide; or by acetylating 11a -acetoxy-progesterone with acetyl chloride and acetic anhydride to form 11a - acetoxy - progesterone - 3 - enol acetate which is then brominated with N-bromoacetamide to form 6-bromo-11a -acetoxy-progesterone which is treated as above with aqueous methanolic hydrochloric or aqueous methanolic silver nitrate and the product saponified with methanolic potassium hydroxide. The above latter process for the preparation of allopregnan-3,6,11,20-tetron may be modified in that the 6,11-diketo-progesterone is prepared by oxidizing 6a ,11a -dihydroxyprogesterone, prepared from 6b ,11a -diacetoxy-progesterone by the process referred to above, with chromic acid. A number of detailed examples are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT777995X | 1954-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB777995A true GB777995A (en) | 1957-07-03 |
Family
ID=11316308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8821/55A Expired GB777995A (en) | 1954-04-01 | 1955-03-25 | Allopregnan-3,6,11,20-tetrone and processes for its preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB777995A (en) |
-
1955
- 1955-03-25 GB GB8821/55A patent/GB777995A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB902293A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| GB777995A (en) | Allopregnan-3,6,11,20-tetrone and processes for its preparation | |
| GB928418A (en) | Preparation of steroid compounds | |
| GB820780A (en) | Cyclopentanophenanthrene derivatives | |
| GB936224A (en) | Novel steroids and their preparation | |
| US2038609A (en) | Compounds containing a mercaptide group and method of producing same | |
| GB744237A (en) | Cyclopentanophenanthrene compounds and process for the production thereof | |
| SU105998A1 (en) | Method for producing pregnadienol-3B-it-20 acetate D5.16 | |
| GB826364A (en) | Cyclopentanopolyhydrophenanthrene compounds | |
| GB978540A (en) | Improvements in or relating to the production of 16ª-alkylthio-17-oxo-steroids | |
| GB936806A (en) | Steroid compounds | |
| GB1019569A (en) | Esters of 1ª‡,2ª‡-methylene-í¸-androstene-3,17ª‰-diol and a process for their manufacture | |
| GB805497A (en) | Steroid intermediates for the preparation of adreno-cortical hormones | |
| GB889311A (en) | Androstenol derivatives | |
| GB773150A (en) | Improvements in or relating to the preparation of steroid compounds | |
| SE329845B (en) | ||
| GB944718A (en) | New steroid compounds and processes for their preparation | |
| ES264322A1 (en) | New steroid compounds and their formation | |
| ES277878A1 (en) | Procedure for the manufacture of 1-alquil-delta-androsten-17-beta-ol-3-onas and its 17 esters (Machine-translation by Google Translate, not legally binding) | |
| GB883310A (en) | Improvements in or relating to hormonal agents | |
| GB979008A (en) | 10-cyano-19-nor-steroids and process for producing 19-norsteroids | |
| GB973897A (en) | New 18-oxygenated pregnane steroids and processes for their preparation | |
| GB768647A (en) | Preparation of cyclopentanopolyhydrophenanthrene compounds | |
| GB977082A (en) | 1ª-methyl-steroids and a process for their manufacture | |
| FR1360135A (en) | Process for the preparation of steroid nitrite ester |