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GB958251A - Improvements in or relating to the preparation of steroid compounds - Google Patents

Improvements in or relating to the preparation of steroid compounds

Info

Publication number
GB958251A
GB958251A GB4028659A GB4028659A GB958251A GB 958251 A GB958251 A GB 958251A GB 4028659 A GB4028659 A GB 4028659A GB 4028659 A GB4028659 A GB 4028659A GB 958251 A GB958251 A GB 958251A
Authority
GB
United Kingdom
Prior art keywords
dibromo
acyloxy
hydroxy
methyl
pregn
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
GB4028659A
Inventor
Alan Gibson Long
Stephen Eardley
George Francis Harold Green
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 GB4028659A priority Critical patent/GB958251A/en
Priority to CH1322360A priority patent/CH392501A/en
Priority to BE597518A priority patent/BE597518A/en
Publication of GB958251A publication Critical patent/GB958251A/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

The invention comprises 21-acyloxy-2, 4-dibromo - 17a - hydroxy - 16b - methyl - 5a -pregn - 9(11) - ene - 3, 20 - diones and a process for the preparation of 21-acyloxy-17a -hydroxy-16b -methyl - pregna - 1, 4, 9(11) - triene - 3, 20-diones by heating a 2, 4-dibromo compound in the presence of lithium, calcium, barium or strontium carbonate and an inert Lewis base containing a tertiary nitrogen atom and having a high dielectric constant (>15), said base being liquid at the temperature of dehydrobromination. The 2, 4-dibromo compounds are themselves prepared by dibromination of a 21-acyloxy-17a -hydroxy-16 b -methyl-5a -pregn-9(11)-ene-3, 20-dione with molecular bromine in an inert solvent. Specified Lewis bases include N,N-dimethylformamide, N, N-diethylacetamide, N,N-dimethyl valeramide, N-formyl piperidine, N-formylmorpholine, N, N, N1, N1-tetramethyl adipamide, N, N-dimethyl cyanamide, and N,N,N1,N1-tetramethylurea, and the dehydrobromination process is preferably carried out in the presence of an alkali metal halide or alkaline earth halide, particularly lithium, sodium or calcium bromide. The mixture of 2,4-dibromo isomers that is obtained may be resolved by chromatography to give the 2a , 4b -dibromo isomer. The invention is illustrated by thirteen detailed examples. Specification 956,272 is referred to.
GB4028659A 1959-11-26 1959-11-26 Improvements in or relating to the preparation of steroid compounds Expired GB958251A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB4028659A GB958251A (en) 1959-11-26 1959-11-26 Improvements in or relating to the preparation of steroid compounds
CH1322360A CH392501A (en) 1959-11-26 1960-11-25 Method of making steroids
BE597518A BE597518A (en) 1959-11-26 1960-11-25 Steroid compounds and their preparation method.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4028659A GB958251A (en) 1959-11-26 1959-11-26 Improvements in or relating to the preparation of steroid compounds

Publications (1)

Publication Number Publication Date
GB958251A true GB958251A (en) 1964-05-21

Family

ID=10414128

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4028659A Expired GB958251A (en) 1959-11-26 1959-11-26 Improvements in or relating to the preparation of steroid compounds

Country Status (3)

Country Link
BE (1) BE597518A (en)
CH (1) CH392501A (en)
GB (1) GB958251A (en)

Also Published As

Publication number Publication date
BE597518A (en) 1961-03-15
CH392501A (en) 1965-05-31

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