GB851741A - Improvements in or relating to the preparation of 6-methyl steroid compounds - Google Patents

Improvements in or relating to the preparation of 6-methyl steroid compounds

Info

Publication number
GB851741A
GB851741A GB2716257A GB2716257A GB851741A GB 851741 A GB851741 A GB 851741A GB 2716257 A GB2716257 A GB 2716257A GB 2716257 A GB2716257 A GB 2716257A GB 851741 A GB851741 A GB 851741A
Authority
GB
United Kingdom
Prior art keywords
compound
acyloxy
spirostan
methyl
preparation
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
GB2716257A
Inventor
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 GB2716257A priority Critical patent/GB851741A/en
Priority to CH6338558A priority patent/CH375346A/en
Publication of GB851741A publication Critical patent/GB851741A/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
    • 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
    • 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 steroid compounds of the general formulae <FORM:0851741/IV(b)/1> <FORM:0851741/IV(b)/2> wherein R represents an acyl group containing up to 10 carbon atoms, and a process for the preparation of 3b -hydroxy-6-methyl-25D-spirost -5-ene and the corresponding 3b -acyloxy compound by reacting 3b -acyloxy-25D-spirost-5-ene with a hypobromous acid or with N-bromoacetamide and perchloric acid to form a 3b -acyloxy-5a -bromo-25D- spirostan-6b -ol, oxidising this compound to form a 3b -acyloxy-5a -bromo-25D-spirostan-6-one, replacing the bromine atom in this compound by hydrogen to form a 3b -acyloxy-5a :25D-spirostan-6-one, reacting this compound with a methyl magnesium halide and reacylating the product to form a 3b -acyloxy-6a -methyl-5a :25D-spirostan-6b -ol, and dehydrating this compound with thionyl chloride in a tertiary base such as pyridine to form the desired 3b -acyloxy compound which may be hydrolysed to the corresponding 3b -hydroxy compound. One detailed example is given illustrating the above process with particular reference to the 3b -acetoxy starting compound, intermediate products and final product which is then hydrolysed as above. Specifications 841,870 and 851,742 are referred to.
GB2716257A 1957-08-28 1957-08-28 Improvements in or relating to the preparation of 6-methyl steroid compounds Expired GB851741A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2716257A GB851741A (en) 1957-08-28 1957-08-28 Improvements in or relating to the preparation of 6-methyl steroid compounds
CH6338558A CH375346A (en) 1957-08-28 1958-08-28 Process for the preparation of methylpregnadien-20-ones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2716257A GB851741A (en) 1957-08-28 1957-08-28 Improvements in or relating to the preparation of 6-methyl steroid compounds

Publications (1)

Publication Number Publication Date
GB851741A true GB851741A (en) 1960-10-19

Family

ID=10255208

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2716257A Expired GB851741A (en) 1957-08-28 1957-08-28 Improvements in or relating to the preparation of 6-methyl steroid compounds

Country Status (2)

Country Link
CH (1) CH375346A (en)
GB (1) GB851741A (en)

Also Published As

Publication number Publication date
CH375346A (en) 1964-02-29

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