GB895340A - Process for the manufacture of halogen pregnenes - Google Patents

Process for the manufacture of halogen pregnenes

Info

Publication number
GB895340A
GB895340A GB26976/58A GB2697658A GB895340A GB 895340 A GB895340 A GB 895340A GB 26976/58 A GB26976/58 A GB 26976/58A GB 2697658 A GB2697658 A GB 2697658A GB 895340 A GB895340 A GB 895340A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
hydroxyl group
free
oxo
group
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
GB26976/58A
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.)
Syntex SA
Original Assignee
Syntex 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 Syntex SA filed Critical Syntex SA
Publication of GB895340A publication Critical patent/GB895340A/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

Abstract

6-Chloropregnanes of the formula <FORM:0895340/IV (b)/1> wherein R1, R2 and R3 are hydrogen, or a free or esterified hydroxyl group, R4 is hydrogen or a methyl group, X is hydrogen, chlorine or fluorine, and Y is two hydrogen atoms, an oxo group or hydrogen and a free or esterified hydroxyl group are prepared from the 3-enol ethers or 3-ketals of the corresponding 6-unsubstituted compounds (which may contain in the 20-position hydrogen and a free or esterified hydroxyl group or a free or ketalised oxo group) by chlorination with chlorine, hypochlorous acid or agents liberating hypochlorous acid, any 5 : 6-dichloro compound formed being dehydrohalogenated, a ketalized oxo group in 3- and/or 20-position or a 20-hydroxyl group being converted into an oxo group the D 4-3-oxo-6b -chloro compound so obtained being isomerised with acid to a D 4-3-oxo-6a -chlor compound and if desired, at any stage of the reaction an esterified hydroxyl group is hydrolysed or a free hydroxyl group is esterified. The process is illustrated by twenty-one examples. The 3-enol ethers required as starting materials are prepared by treating the appropriate D 4-3-ketone with ethyl or propyl orthoformate and concentrated sulphuric acid or p-toluene sulphnic acid in ethanol-dioxane. The preparation of hydrocortisone-11-trifluoroacetate 21-acetate is also detailed. Specification 834,372 is referred to.
GB26976/58A 1957-08-30 1958-08-21 Process for the manufacture of halogen pregnenes Expired GB895340A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX895340X 1957-08-30

Publications (1)

Publication Number Publication Date
GB895340A true GB895340A (en) 1962-05-02

Family

ID=19743144

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26976/58A Expired GB895340A (en) 1957-08-30 1958-08-21 Process for the manufacture of halogen pregnenes

Country Status (1)

Country Link
GB (1) GB895340A (en)

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