GB908674A - Preparation of 17ª--acyloxy-6ª--methyl-16-methylenepregn-4-ene-3,20-diones - Google Patents
Preparation of 17ª--acyloxy-6ª--methyl-16-methylenepregn-4-ene-3,20-dionesInfo
- Publication number
- GB908674A GB908674A GB2256360A GB2256360A GB908674A GB 908674 A GB908674 A GB 908674A GB 2256360 A GB2256360 A GB 2256360A GB 2256360 A GB2256360 A GB 2256360A GB 908674 A GB908674 A GB 908674A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acyloxy
- epoxy
- give
- compound
- 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 (1) a process for preparing steroids of the formula <FORM:0908674/IV (b)/1> (wherein R is an acyl group of at most 10 carbon atoms) which comprises oxidizing with an organic per-acid 3b -hydroxy- or a 3b -acyloxy - 16a ,17a - epoxy - 16b - methylpregn-5-en-20-one (II) to the corresponding 5a ,6a ,16a , 17a -bis-epoxide (III), reducing the 20-ketogroup to a 20-hydroxyl-group and acylating the product if desired, treating the resulting dihydroxy- or diacyloxy-compound (IV) with methyl magnesium halide to give 16a ,17a -epoxy - 6b ,16b - dimethylpregnane - 3b ,5a ,20-triol (V), oxidizing this to the corresponding 3,20-dione (VI), dehydrating and isomerizing this to give 16a ,17a -epoxy-6a ,16b -dimethyl-pregn-4-ene-3,20-dione, treating this with a carboxylic acid anhydride in presence of an acidic catalyst to give a 3,17a -diacyloxy-6-methyl-16-methylene-pregn-3,5-dien-20-one and selectively hydrolysing the acyloxy group at position 3; and (2) as new steroids compounds III wherein the 3-group is hydroxy and acetoxy, compounds IV wherein the 3,20-groups are dihydroxy and diacetoxy, compound V and compound VI. Detailed examples are given. Specifications 858,033 and 887,684 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2256360A GB908674A (en) | 1960-06-28 | 1960-06-28 | Preparation of 17ª--acyloxy-6ª--methyl-16-methylenepregn-4-ene-3,20-diones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2256360A GB908674A (en) | 1960-06-28 | 1960-06-28 | Preparation of 17ª--acyloxy-6ª--methyl-16-methylenepregn-4-ene-3,20-diones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB908674A true GB908674A (en) | 1962-10-24 |
Family
ID=10181453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2256360A Expired GB908674A (en) | 1960-06-28 | 1960-06-28 | Preparation of 17ª--acyloxy-6ª--methyl-16-methylenepregn-4-ene-3,20-diones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB908674A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0911315B1 (en) * | 1997-10-21 | 2003-06-11 | Givaudan SA | Beta-ketoester |
-
1960
- 1960-06-28 GB GB2256360A patent/GB908674A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0911315B1 (en) * | 1997-10-21 | 2003-06-11 | Givaudan SA | Beta-ketoester |
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