GB719226A - Process of reducing a ketone grouping in a keto-substituted steroid compound - Google Patents

Process of reducing a ketone grouping in a keto-substituted steroid compound

Info

Publication number
GB719226A
GB719226A GB26865/51A GB2686551A GB719226A GB 719226 A GB719226 A GB 719226A GB 26865/51 A GB26865/51 A GB 26865/51A GB 2686551 A GB2686551 A GB 2686551A GB 719226 A GB719226 A GB 719226A
Authority
GB
United Kingdom
Prior art keywords
keto
cyano
pregnene
hydroxy
oximino
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
GB26865/51A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB719226A publication Critical patent/GB719226A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes 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

A ketone grouping in a keto-substituted steroid compound containing at least one unsaturated carbon-nitrogen linkage is reduced, without substantially affecting said linkage, by reacting said keto-substituted steroid compound with an alkali metal borohydride thereby forming the corresponding hydroxy-substituted steroid compound. As alkali metal borohydride there may be used sodium or lithium borohydrides. The reaction may be effected in an organic solvent, e.g. tetrahydrofuran, in the temperature range 0 DEG to 70 DEG C. As starting materials there may be used D 17-11-keto-20-cyano - pregnene; D 17 - 3,11 - diketo - 20 - cyano - pregnene; D 17 - 3 - hydroxy - 11 - keto - 20 - cyano - pregnene; D 17 - 3,11 - diketo - 20 - cyano - 21 - hydroxy - pregnene; D 17 - 3,21 - dihydroxy - 11 - keto - 20 - cyano - pregnene; D 17 - 3 - hydroxy - 11 - keto - 20 - cyano - 21 - acyloxy - pregnenes; D 17 - 3,11 - diketo - 20 - cyano - 21 - acetoxy - pregnene; D 17 - 3,11 - diketo - 20 - cyano - 21 - acyloxy - pregnenes as well as D 17-11-keto-20-cyano compounds containing additional unsaturation such as D 17-3-(oximino, semicarbazido or arylhydrazino)-11-keto - 20 - cyano - pregnenes; D 17 - 3 - (oximino, semicarbazido or arylhydrazino)-11-keto-20 - cyano - 21 - hydroxy - pregnene; or D 17-3-(oximino, semicarbazido or arylhydrazino)-11-keto - 20 - cyano - 21 - acyloxy - pregnene. More generally the starting materials are 11-keto steroids containing at least one unsaturated carbon-nitrogen linkage, e.g. an oximino, semi-carbazido or arylhydrazino group.
GB26865/51A 1950-11-25 1951-11-16 Process of reducing a ketone grouping in a keto-substituted steroid compound Expired GB719226A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US719226XA 1950-11-25 1950-11-25

Publications (1)

Publication Number Publication Date
GB719226A true GB719226A (en) 1954-12-01

Family

ID=22104452

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26865/51A Expired GB719226A (en) 1950-11-25 1951-11-16 Process of reducing a ketone grouping in a keto-substituted steroid compound

Country Status (1)

Country Link
GB (1) GB719226A (en)

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