GB880363A - Improvements in or relating to steroid compounds - Google Patents

Improvements in or relating to steroid compounds

Info

Publication number
GB880363A
GB880363A GB14952/60A GB1495260A GB880363A GB 880363 A GB880363 A GB 880363A GB 14952/60 A GB14952/60 A GB 14952/60A GB 1495260 A GB1495260 A GB 1495260A GB 880363 A GB880363 A GB 880363A
Authority
GB
United Kingdom
Prior art keywords
cholestadiene
cholesterone
dehydrocholesterol
dinitrobenzoate
bromo
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
GB14952/60A
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.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie 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 Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB880363A publication Critical patent/GB880363A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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

The invention comprises 19-nor-7-dehydrocholesterol and esters thereof such as the 3,5-dinitrobenzoate thereof, 19-nor-3-acetoxy-D 3,5,7-cholestatriene, 19-nor-D 4,6-cholestadiene-3-one and 19-nor-6-bromo-cholesterone, and a process for the preparation of 19-nor-7-dehydrocholesterol by reducing an enol ester of 19-nor-D 4,6-cholestadiene-3-one with an alkali metal borohydride. The above process may be modified in that 19-nor-D 4,6-cholestadiene-3-one from which the enol ester is produced is obtained by dehydrobrominating 6-bromo-19-nor-cholesterone e.g. by means of lithium bromide and lithium carbonate in the presence of dimethyl formomide, and the 6-bromo-19-nor-cholesterone is prepared by brominating an enol ester of 19-nor-chlosterone which may be prepared by a method described and claimed in Specification 880,362. The 19-nor-7-dehydrocholesterol prepared by the above method may be purified by converting it into its 3,5-dinitrobenzoate and then saponifying the dinitrobenzoate. The enol ester is preferably the acetic acid ester and is obtainable by the action of a mixture of acetic anhydride and acetyl chloride. 19-nor-D 4,6-cholestadiene-3-one may also be obtained by oxidising 19-nor-cholesterol with manganese dioxide. Detailed examples are given. Specification 832,244 also is referred to.
GB14952/60A 1957-06-14 1958-05-21 Improvements in or relating to steroid compounds Expired GB880363A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR880363X 1957-06-14

Publications (1)

Publication Number Publication Date
GB880363A true GB880363A (en) 1961-10-18

Family

ID=9364448

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14952/60A Expired GB880363A (en) 1957-06-14 1958-05-21 Improvements in or relating to steroid compounds

Country Status (1)

Country Link
GB (1) GB880363A (en)

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