GB794487A - Steroid compounds and process for their production - Google Patents

Steroid compounds and process for their production

Info

Publication number
GB794487A
GB794487A GB15419/56A GB1541956A GB794487A GB 794487 A GB794487 A GB 794487A GB 15419/56 A GB15419/56 A GB 15419/56A GB 1541956 A GB1541956 A GB 1541956A GB 794487 A GB794487 A GB 794487A
Authority
GB
United Kingdom
Prior art keywords
methyl
pregnadien
dione
dihydroxy
lower alkyl
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
GB15419/56A
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 GB794487A publication Critical patent/GB794487A/en
Expired legal-status Critical Current

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

794,487. Steroids. UPJOHN CO. May 17, 1956 [May 23, 1955], No. 15419/56. Class 2 (3). The invention comprises compounds of the general formula. and 21-lower acyloxy esters thereof, wherein the acyl radical is that of a hydrocarbon carboxylic acid containing from 1-12 carbon atoms and lower alkyl contains 1-8 carbon atoms, and the production thereof by oxidatively hydroxylating an 11α - lower alkyl - 11#, 21 - dihydroxy - 4,17(2) - pregnadien - 3 - one or a 21 - ester thereof with osmium tetroxide and an oxidizing agent, e.g. hydrogen peroxide, peracids, alkyl peroxides, and amine oxide peroxides. Preferably 2-3 molar equivalents of the oxidizing agent are used together with less than 0.05 molar equivalent of osmium tetroxide calculated on the starting steroid in tertiary-butyl alcohol at about room temperature. The 11α-lower alkyl- 11#,21 - dihydroxy - 4,17(20) - pregnadien - 3 - one or 21-ester thereof is obtained by alkylating a 3-cyclic ketal or 3-enol ether of a 21-hydrocarbonoxy - 5,17(20) - pregnadiene - 3,11 - dione with a lower alkyl lithium to produce the corresponding 11α-alkyl compound, hydrolysing the 3-keto protected group and esterifying with a hydrocarbon carboxylic acid containing 1-12 carbon atoms. As alkylating agents there may be used methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, or octyl lithium. Hydrolysis may be effected with aqueous hydrochloric or sulphuric acids. Examples describe the preparation of the 3-ethylene glycol ketal of 11α- methyl - 11# - hydroxy - 21 - triphenylmethoxy- 5,17(20) - [cis] - pregnadien - 3 - one, 11α - methyl - 11#,21 - dihydroxy - 4,17(20) - [cis] - pregnadien - 3 - one, 11 - # - hydroxy - 11α - methyl - 21 - acetoxy - 4,17(20) - [cis] - pregnadien-3-one and other 21-esters thereof; 11α- methyl - 11#,17α - dihydroxy - 21 - acetoxy - 4 - pregnene - 3,20 - dione, and 11α - methyl - 11#,17α,21 - trihydroxy - 4 - pregnene - 3,20 - dione. 21 - Hydroxy - 5,17(20) - pregnadiene - 3,11-dione is obtained by ketalizing a 21-acyloxy - 4,17(20) - pregnadiene - 3,20 - dione and subsequently hydrolysing the 21-acyloxy group. Specifications 749,201 and 794,485 are referred to.
GB15419/56A 1955-05-23 1956-05-17 Steroid compounds and process for their production Expired GB794487A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US794487XA 1955-05-23 1955-05-23

Publications (1)

Publication Number Publication Date
GB794487A true GB794487A (en) 1958-05-07

Family

ID=22150629

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15419/56A Expired GB794487A (en) 1955-05-23 1956-05-17 Steroid compounds and process for their production

Country Status (1)

Country Link
GB (1) GB794487A (en)

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