GB890474A - Improvements in or relating to novel steroids and the manufacture thereof - Google Patents

Improvements in or relating to novel steroids and the manufacture thereof

Info

Publication number
GB890474A
GB890474A GB11609/60A GB1160960A GB890474A GB 890474 A GB890474 A GB 890474A GB 11609/60 A GB11609/60 A GB 11609/60A GB 1160960 A GB1160960 A GB 1160960A GB 890474 A GB890474 A GB 890474A
Authority
GB
United Kingdom
Prior art keywords
methyl
produce
fluoro
compound
hydroxy
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
GB11609/60A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB890474A publication Critical patent/GB890474A/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 a compound of the formula <FORM:0890474/IV (b)/1> wherein R is H or the acyl radical of a hydrocarbon carboxylic acid containing from 1-12 carbon atoms and processes for the preparation thereof, by reacting 16a -methylpregnenolone or 16b -methylpregnenolone with diethyloxalate and sodium methoxide to produce the sodium enolate of 16-methyl-21-ethoxyoxalylpregnenolone, converting the latter compound with potassium acetate and 2 moles of bromine to produce 16-methyl-21,21-dibromo-21-ethoxyoxalyl-pregnenolone, treating this compound with sodium or potassium alkoxide to produce 3b - hydroxy - 16 - methyl - 5, 17 (20) - pregnadien - 21-oic acid lower alkyl ester, epoxidising to produce 3b - hydroxy - 5a , 6a - epoxy - 16 - methyl-17(20)-pregnen-21-oic acid lower alkyl ester, reacting with HF, oxidising to obtain the 3-keto derivative, ketalising the 3-keto-5a -hydroxy - 6b - fluoro - 16 - methyl - 17 (20) - pregnen-21-oic acid lower alkyl ester reducing the side chain of the 3-ketalised-3-keto-5a -hydroxy-6b - fluoro - 16 - methyl - 17 (20) - pregnen - 21 - oic acid lower alkyl ester with an alkali metal aluminium hydride, esterifying to produce the corresponding 21-ester and then subjecting this compound to oxidative hydroxylation to produce the corresponding 3-ketalised 5a ,17a ,21-trihydroxy - 6b - fluoro - 16 - methylpregnane - 3,20-dione 21-acylate and hydrolysing this compound under acidic conditions. Hydrolysis may be effected with hydrogen chloride in the presence of chloroform and a lower alkanol. The 21-acylate group, if retained, may be hydrolysed with a base. Products claimed are 6a -fluoro-16a -methyl - 17a , 21 - dihydroxy - 4 - pregnene - 3, 20 - dione, 6a - fluoro - 16a - methyl - 17a , 21 - dihydroxy - 4 - pregnene - 3, 20 - dione 21 - acetate and the corresponding 16b -methyl compounds. Specification 724,094 is referred to.
GB11609/60A 1959-05-11 1960-04-01 Improvements in or relating to novel steroids and the manufacture thereof Expired GB890474A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US890474XA 1959-05-11 1959-05-11

Publications (1)

Publication Number Publication Date
GB890474A true GB890474A (en) 1962-02-28

Family

ID=22215316

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11609/60A Expired GB890474A (en) 1959-05-11 1960-04-01 Improvements in or relating to novel steroids and the manufacture thereof

Country Status (2)

Country Link
DE (1) DE1168902B (en)
GB (1) GB890474A (en)

Also Published As

Publication number Publication date
DE1168902B (en) 1964-04-30

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