GB934705A - Improvements in or relating to steroids - Google Patents

Improvements in or relating to steroids

Info

Publication number
GB934705A
GB934705A GB900160A GB900160A GB934705A GB 934705 A GB934705 A GB 934705A GB 900160 A GB900160 A GB 900160A GB 900160 A GB900160 A GB 900160A GB 934705 A GB934705 A GB 934705A
Authority
GB
United Kingdom
Prior art keywords
methyl
ketone group
pregnan
trihydroxy
group
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
GB900160A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB934705A publication Critical patent/GB934705A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • 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

The invention comprises 3a ,11a ,17a -trihydroxy-16a -methyl-pregnan-20-one, the 20-ethylenedioxy derivative thereof and the preparation thereof by reacting a 3-acyloxy-16b -methyl-16a ,17a -epoxypregnane-11,20-dione having a protected 20-ketone group, with lithium in the presence of an aliphatic amine having 1-6 carbon atoms, thus bringing about simultaneous severance of the 16,17-epoxide link, inversion of the steric position of the 16-methyl group, reduction of the 11-ketone group and saponification of the 3-acyloxy substituent, so as to form 3a ,11a ,17a -trihydroxy-16a -methyl-pregnan-20-one, the ketone group of which is protected, liberating the 20-ketone group thereof to yield 3a ,11a ,17a -trihydroxy-16a -methyl-pregnan-20-one and oxidising selectively the 3a -hydroxy group of this latter compound. As aliphatic amine, methylamine may be used. Oxidation may be effected with N-bromosuccinimide. Specifications 874,780, 934,701 and 934,703 are referred to.
GB900160A 1959-03-27 1960-03-14 Improvements in or relating to steroids Expired GB934705A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR790689A FR1234741A (en) 1959-03-27 1959-03-27 Process for the preparation of 11, 17 dihydroxy pregnanes 3, 20-methylated diones

Publications (1)

Publication Number Publication Date
GB934705A true GB934705A (en) 1963-08-21

Family

ID=8713045

Family Applications (1)

Application Number Title Priority Date Filing Date
GB900160A Expired GB934705A (en) 1959-03-27 1960-03-14 Improvements in or relating to steroids

Country Status (5)

Country Link
BE (1) BE589064A (en)
CH (1) CH394182A (en)
ES (1) ES256862A1 (en)
FR (1) FR1234741A (en)
GB (1) GB934705A (en)

Also Published As

Publication number Publication date
CH394182A (en) 1965-06-30
FR1234741A (en) 1960-10-19
ES256862A1 (en) 1960-06-01
BE589064A (en) 1960-09-26

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