GB750920A - Improvements in or relating to the preparation of new steroid substances - Google Patents

Improvements in or relating to the preparation of new steroid substances

Info

Publication number
GB750920A
GB750920A GB2384453A GB2384453A GB750920A GB 750920 A GB750920 A GB 750920A GB 2384453 A GB2384453 A GB 2384453A GB 2384453 A GB2384453 A GB 2384453A GB 750920 A GB750920 A GB 750920A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
spirost
ene
product
acetoxy
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
GB2384453A
Inventor
John Warcup Cornforth
Joseph Elks
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.)
GNRD Patent Holdings Ltd
Original Assignee
GNRD Patent Holdings Ltd
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 GNRD Patent Holdings Ltd filed Critical GNRD Patent Holdings Ltd
Priority to GB2384453A priority Critical patent/GB750920A/en
Publication of GB750920A publication Critical patent/GB750920A/en
Expired legal-status Critical Current

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
    • 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 compounds of the formula <FORM:0750920/IV(a)/1> (where X is hydrogen or bromine, and R is a hydroxyl group or an esterified hydroxyl group) and a process for their preparation by treating the corresponding 11a -bromo-12a -hydroxy compounds in which X is bromine with zinc and an aliphatic acid containing from 2-6 carbon atoms. Elimination of the 23-bromine atom occurs only when vigorous debromination conditions are used. The 11 : 23-dibromo-12a -hydroxy intermediates are prepared from the corresponding 12-keto compounds by reduction with lithium aluminium hydride (preferably in ether at 0 DEG C.) or with sodium borohydride (e.g. in aqueous ethanol, dioxan, ethyl acetate or methylene chloride/ethanol), yielding a mixture of 12a - and 12b -hydroxy epimers, which may be used directly or the required 12a -epimer separated by chromatography or alumina. A 3-acyloxy group may be hydrolysed during the reduction and re-acylation is then desirable prior to the debromination step. In examples (1) 11a : 23-dibromohecogenin acetate is reduced with lithium aluminium hydride in ether, and the crude reduction product is esterified with acetic anhydride/pyridine and warmed with zinc powder and acetic acid to produce 3b -acetoxy - 23 - bromo - 5a - 22a - spirost - 11-ene; (2) 11a : 23-dibromohecogenin acetate is reduced with sodium borohydride in aqueous ethanol containing sodium bicarbonate, and the crude product is heated with zinc dust in boiling acetic acid to give 3b -acetoxy-5a -22a-spirost-11-ene; (3) as in (2) except that the crude reduction product is chromatographed on alumina to isolate 3b -acetoxy-11a : 23-dibromo-12a - hydroxy - 5a - 22a - spirostane from the mixture of isomers obtained; (4) the product of (2) is hydrolysed by refluxing with aqueous ethanolic caustic soda, yielding 3b -hydroxy-5a -22a - spirost - 11 - ene; (5) the product of (1) similarly yields 3b -hydroxy-23-bromo-5a -22a-spirost-11-ene.
GB2384453A 1953-08-28 1953-08-28 Improvements in or relating to the preparation of new steroid substances Expired GB750920A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2384453A GB750920A (en) 1953-08-28 1953-08-28 Improvements in or relating to the preparation of new steroid substances

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2384453A GB750920A (en) 1953-08-28 1953-08-28 Improvements in or relating to the preparation of new steroid substances

Publications (1)

Publication Number Publication Date
GB750920A true GB750920A (en) 1956-06-20

Family

ID=10202223

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2384453A Expired GB750920A (en) 1953-08-28 1953-08-28 Improvements in or relating to the preparation of new steroid substances

Country Status (1)

Country Link
GB (1) GB750920A (en)

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