GB743487A - Hydroxysteroid ketals - Google Patents

Hydroxysteroid ketals

Info

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
Application number
GB64/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB743487A publication Critical patent/GB743487A/en
Expired legal-status Critical Current

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

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.
GB64/53A 1952-01-02 1953-01-01 Hydroxysteroid ketals Expired GB743487A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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