GB987576A - Process for the manufacture of 16ª‡-alkyl-20:21-ketols of the pregnane series - Google Patents
Process for the manufacture of 16ª‡-alkyl-20:21-ketols of the pregnane seriesInfo
- Publication number
- GB987576A GB987576A GB2616161A GB2616161A GB987576A GB 987576 A GB987576 A GB 987576A GB 2616161 A GB2616161 A GB 2616161A GB 2616161 A GB2616161 A GB 2616161A GB 987576 A GB987576 A GB 987576A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrolysed
- acetate
- ketols
- aldosterone
- 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
- 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 the preparation of 16a -alkyl-20,21-ketols of the pregnane series wherein a D 16 -20-oxo-pregnene-21-acid ester is reacted in the presence of a cuprous halide with an alkyl-metal compound, the resulting D 17 -20-enolate-metal salt, if desired after esterification of the enolic hydroxyl group, is reduced with a complex metal hydride in a non-hydroxylic solvent, the 20-enol derivative is hydrolysed to form the free 20-ketone, and, if desired, the 21-hydroxyl group is esterified and any ketal or acetal groups present are hydrolysed; and (2) steroids of the formula <FORM:0987576/C2/1> (wherein R1 is an alkyl group of at most 7 carbon atoms, and R2 and R3 are free, etherified or esterified hydroxyl groups) and the corresponding D 5 -3-alkylene-ketals. The products of the above process are stated to contain a certain proportion of the corresponding 16-unsubstituted compound. In an example D 5-16-3-ethylenedioxy - 11b , 18 - oxido - 18 - tetrahydropyranyloxy - 20 - oxo - pregnadiene - 21 - acid methyl ester is converted to 16a -methylaldosterone acetate (and some aldosterone acetate), and to esters with other acids, an extensive list of which is provided; and the acetate is hydrolysed to 16a -methyl-aldosterone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH821760A CH397666A (en) | 1960-07-19 | 1960-07-19 | Process for the preparation of 16a-alkyl-20,21-ketols of the pregnane series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB987576A true GB987576A (en) | 1965-03-31 |
Family
ID=4336944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2616161A Expired GB987576A (en) | 1960-07-19 | 1961-07-19 | Process for the manufacture of 16ª‡-alkyl-20:21-ketols of the pregnane series |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH397666A (en) |
| GB (1) | GB987576A (en) |
-
1960
- 1960-07-19 CH CH821760A patent/CH397666A/en unknown
-
1961
- 1961-07-19 GB GB2616161A patent/GB987576A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH397666A (en) | 1965-08-31 |
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