GB923531A - Steroids - Google Patents
SteroidsInfo
- Publication number
- GB923531A GB923531A GB691059A GB691059A GB923531A GB 923531 A GB923531 A GB 923531A GB 691059 A GB691059 A GB 691059A GB 691059 A GB691059 A GB 691059A GB 923531 A GB923531 A GB 923531A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethylene glycol
- cyano
- allopregnene
- reacting
- preparation
- 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
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises steroids of the general formulae <FORM:0923531/IV(a)/1> and <FORM:0923531/IV(a)/2> wherein Z represents a cyano or an acyl group and X represents oxygen and, when Z represents a cyano group X also represents an ethylenedioxy group, and a process for the preparation of D 2- and D 3-allopregnene-3-cyano-20-one by reacting allopregnan3b -ol-20-one-3-acylate with ethylene glycol in the presence of an acid catalyst to form the corresponding 20-ethylene glycol ketal, hydrolysing the ester group at the 3-position of the latter compound to form the 20-ethylene glycol ketal of allopregnan-3b -ol-20-one, oxidising this compound to form allopregnane-3,20-dione 20-ethylene glycol ketal, reacting this compound with the cyanhydrin of a lower aliphatic ketone to form allopregnane-3,20-dione 20-ethylene glycol ketal 3-cyanohydrins, and dehydrating the cyanohydrins to obtain a mixture of the desired D 2and D 3-allopregnene-3-cyano-20-ones, the preparation of D 2- and/or D 3-allopregnene-3-cyano-20-one 20-ethylene glycol ketal by reacting D 2- and/or D 3-allopregnene-3-cyano-20-one with an excess of ethylene glycol in the presence of ethylene glycol in the presence of catalytic amounts of p-toluene sulphonic acid; and the preparation of D 2-and/or D 3-allopregnen-20-one-3-alkyl ketone by reacting D 2- and/or D 3-allopregnene-3-cyano-20-one with an alkyl magnesium halide to form the corresponding 3-ketoimines, and treating the ketoimines with dilute mineral acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB691059A GB923531A (en) | 1959-02-27 | 1959-02-27 | Steroids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB691059A GB923531A (en) | 1959-02-27 | 1959-02-27 | Steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB923531A true GB923531A (en) | 1963-04-10 |
Family
ID=9823059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB691059A Expired GB923531A (en) | 1959-02-27 | 1959-02-27 | Steroids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB923531A (en) |
-
1959
- 1959-02-27 GB GB691059A patent/GB923531A/en not_active Expired
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