GB1003081A - A process for the preparation of 16ª‰-methyl steroids - Google Patents

A process for the preparation of 16ª‰-methyl steroids

Info

Publication number
GB1003081A
GB1003081A GB2808661A GB2808661A GB1003081A GB 1003081 A GB1003081 A GB 1003081A GB 2808661 A GB2808661 A GB 2808661A GB 2808661 A GB2808661 A GB 2808661A GB 1003081 A GB1003081 A GB 1003081A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
keto
methyl
steroids
iridium
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
GB2808661A
Inventor
Gordon Hanley Phillipps
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.)
Glaxo Group Ltd
Original Assignee
Glaxo Group 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 Glaxo Group Ltd filed Critical Glaxo Group Ltd
Priority to GB2808661A priority Critical patent/GB1003081A/en
Priority to CH903862A priority patent/CH425780A/en
Priority to BR14177162A priority patent/BR6241771D0/en
Publication of GB1003081A publication Critical patent/GB1003081A/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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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

17a - Hydroxy - 20 - keto - 16b - methyl steroids are prepared by hydrogenating 17a -hydroxy - 20 - keto - 16 - methylene steroids in the presence of an iridium catalyst. The iridium may be unsupported or supported on, for example, barium sulphate, kieselguhr or calcium carbonate, and it may be formed in situ by reduction of iridium dioxide. The 16b -methyl steroid may be separated from concomitantly formed 16a -methyl steroid by, for example, repeated crystallization. The steroids may contain, for example, 3-acyloxy, -hydroxy or -keto groups; 11-acyloxy, -hydroxy or -keto groups; 9,11-dichloro substituents; D 9(11)-double bonds; and 5a - or 5b -hydrogen atoms, in addition to the normal 17-substituents of pregnane compounds. Reduction of some of these groups, e.g. 3-keto, may occur during the process, but D 9(11)-double bonds are, in general, not effected. Examples are provided. 11b ,21 - Diacetoxy - 3b ,17a - dihydroxy - 16 - methylene - 5a - pregnan - 20 - one is prepared from 3b ,11b -diacetoxy-5a -pregn-16-en-20-one by the steps of reaction with diazomethane, pyrolysis to form the 16-methyl-16(17)-ene compound, epoxidation, rearrangement with acid to a 17a -hydroxy-16-methylen compound, bromination to a 21-bromide and reaction with potassium acetate. Specifications 956,271, 956,272, and 1,003,082 are referred to.
GB2808661A 1961-08-02 1961-08-02 A process for the preparation of 16ª‰-methyl steroids Expired GB1003081A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB2808661A GB1003081A (en) 1961-08-02 1961-08-02 A process for the preparation of 16ª‰-methyl steroids
CH903862A CH425780A (en) 1961-08-02 1962-07-27 Process for the preparation of 17a-hydroxy-20-keto-16B-methyl-steroids
BR14177162A BR6241771D0 (en) 1961-08-02 1962-08-02 PROCESS FOR THE PRODUCTION OF 17 ALPHA-HYDROXY-20 CETO-16 BETA METHYL STEROIDS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2808661A GB1003081A (en) 1961-08-02 1961-08-02 A process for the preparation of 16ª‰-methyl steroids

Publications (1)

Publication Number Publication Date
GB1003081A true GB1003081A (en) 1965-09-02

Family

ID=10270051

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2808661A Expired GB1003081A (en) 1961-08-02 1961-08-02 A process for the preparation of 16ª‰-methyl steroids

Country Status (3)

Country Link
BR (1) BR6241771D0 (en)
CH (1) CH425780A (en)
GB (1) GB1003081A (en)

Also Published As

Publication number Publication date
BR6241771D0 (en) 1973-07-10
CH425780A (en) 1966-12-15

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