GB887684A - 16-methylene steroids - Google Patents

16-methylene steroids

Info

Publication number
GB887684A
GB887684A GB32720/59A GB3272059A GB887684A GB 887684 A GB887684 A GB 887684A GB 32720/59 A GB32720/59 A GB 32720/59A GB 3272059 A GB3272059 A GB 3272059A GB 887684 A GB887684 A GB 887684A
Authority
GB
United Kingdom
Prior art keywords
acyloxy
hydroxy
give
methylenepregn
compound
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
GB32720/59A
Inventor
David Neville Kirk
Vladimir Petrow
David Morton Williamson
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals 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 BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB32720/59A priority Critical patent/GB887684A/en
Publication of GB887684A publication Critical patent/GB887684A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises (1) the 3-monoacetate, the 17-monoacetate and the 3,17-diacetate of 3b : 17a - dihydroxy - 16 - methylenepregn - 5 - en-20-one; and (2) a process for the preparation of 17a -hydroxy- or a 17a -acyloxy-16-methylene-pregn-4-ene-3,20-dione (wherein the acyloxy group contains at most 10 carbon atoms) which comprises oxidizing with an alkaline peroxidizing agent 3b -hydroxy- or a 3b -acyloxy-16-methyl-pregna-5, 16-dien-20-one to the corresponding 3b -hydroxy-16a : 17a -epoxide, acylating this, treating the 3b -acyloxy (wherein the acyloxy group contains at most 10 carbon atoms) compound with a source of hydrogen ions in an inert non-polar solvent to give a 3b -acyloxy-17a -hydroxy-16-methylenepregn-5-en-20-one, acylating this to give the 3b : 17a -diacylate, preferentially hydrolysing this to give a 17a -acyloxy-3b -hydroxy-16-methylenepregn-5-en-20-one, oxidizing this, e.g. by the Oppenauer method, to give the required 17a -acyloxy compound, and, if desired, hydrolysing this to the required 17a -hydroxy compound. Examples are given. Reference has been directed by the Comptroller to Specification 857,114.
GB32720/59A 1959-09-25 1959-09-25 16-methylene steroids Expired GB887684A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB32720/59A GB887684A (en) 1959-09-25 1959-09-25 16-methylene steroids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB32720/59A GB887684A (en) 1959-09-25 1959-09-25 16-methylene steroids

Publications (1)

Publication Number Publication Date
GB887684A true GB887684A (en) 1962-01-24

Family

ID=10343014

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32720/59A Expired GB887684A (en) 1959-09-25 1959-09-25 16-methylene steroids

Country Status (1)

Country Link
GB (1) GB887684A (en)

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