GB743487A - Hydroxysteroid ketals - Google Patents
Hydroxysteroid ketalsInfo
- Publication number
- GB743487A GB743487A GB64/53A GB6453A GB743487A GB 743487 A GB743487 A GB 743487A GB 64/53 A GB64/53 A GB 64/53A GB 6453 A GB6453 A GB 6453A GB 743487 A GB743487 A GB 743487A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxypregnane
- diketal
- dione
- lithium
- diketals
- 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
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 11b - hydroxypregnane-3 : 20-dione 3 : 20-alkanediol diketals of the general formula <FORM:0743487/IV(a)/1> (wherein R represents a hydrogen atom or an alkyl radical containing from one to six carbon atoms, and n is one or two, subject to the restriction that when n is two, R contains not more than five carbon atoms), together with a process for their preparation by reduction of the corresponding 11-keto derivatives in an organic solvent at a temperature between 0 DEG C. and the reflux temperature of the reaction mixture. Specified reducing agents are lithium aluminium hydride, sodium borohydride, lithium borohydride, and hydrogen in the presence of catalysts, e.g. Raney nickel or platinum. In an example: pregnane-3 : 11 : 20-trione-3 : 20-ethylene glycol diketal in benzene is refluxed with ethereal lithium aluminium hydride and the product treated with ice to yield 11b -hydroxypregnane - 3 : 20 - dione - 3 : 20 - ethyllene glycol diketal, which may then be hydrolysed to 11b -hydroxypregnane-3 : 20-dione. The same diketal is also prepared using as reducing agents lithium borohydride in aqueous ethanol, and sodium borohydride in aqueous isopropanol. Other 11b -hydroxy-3 : 20-diketals mentioned are those derived from propane-, butane-, pentane-, hexane-, heptane-, octane- and 4-methylpentane-1 : 3-diols and from propane-, octane- and 3-methylbutane-1 : 2-diols. Specifications 743,484 and 743,486 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US743487XA | 1952-01-02 | 1952-01-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB743487A true GB743487A (en) | 1956-01-18 |
Family
ID=22119080
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB64/53A Expired GB743487A (en) | 1952-01-02 | 1953-01-01 | Hydroxysteroid ketals |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB743487A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3088945A (en) * | 1958-08-07 | 1963-05-07 | Merck & Co Inc | Process for the preparation of 12alpha-alkyl steroids |
-
1953
- 1953-01-01 GB GB64/53A patent/GB743487A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3088945A (en) * | 1958-08-07 | 1963-05-07 | Merck & Co Inc | Process for the preparation of 12alpha-alkyl steroids |
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