PROCESS FOR PRODUCING 11BETA-HYDROXYANDROST-4-ENE-3,17-DIONE

PROCESS FOR PRODUCING 11BETA-HYDROXYANDROST-4-ENE-3,17-DIONE

17b - Hydroxy - 4,9(11) - androstadien - 3-one is obtained in a process which comprises cleaving the 17-side chain using acidic lead tetracetate or periodic acid, from 11b ,17a ,20,21-tetrahydroxy - 4 - pregnen - 3 - one 21 - acetate (or the 11a -hydroxy epimer), to form the corresponding 17-ketone,...

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Bibliographische Detailangaben
1. Verfasser: BRADFORD H. WALKER
Format: Patent
Sprache:eng
Schlagworte:
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
STEROIDS
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Zusammenfassung:17b - Hydroxy - 4,9(11) - androstadien - 3-one is obtained in a process which comprises cleaving the 17-side chain using acidic lead tetracetate or periodic acid, from 11b ,17a ,20,21-tetrahydroxy - 4 - pregnen - 3 - one 21 - acetate (or the 11a -hydroxy epimer), to form the corresponding 17-ketone, reacting the latter with N-bromoacetamide and sulphur dioxide to produce the corresponding 9(11)-dehydro product, protecting the 3-keto group by means of a 3-enamine, 3-ketal or 3-enol lower alkyl ether, and reducing the 17-ketone group, followed by the removal of the 3-ketone protecting group.