Production of 7 beta-hydroxy-dehydroepiandrosterone, comprises, e.g. selective oximation and reduction process involving 3-O-acetyl-7-oxo-dehydroepiandrosterone

Production of 7beta-hydroxy-dehydroepiandrosterone (I), comprises: (1) protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone (II) using an optionally O-protected hydrazine; (2) reduction of the 7-keto group of the obtained 17-oxime (IV) using alkali metal borohydride; (3) deprot...

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Hauptverfasser:	CAVEZZA ALEXANDRE, RADISSON XAVIER, PICHAUD PATRICK
Format:	Patent
Sprache:	eng ; fre
Schlagworte:	CHEMISTRY METALLURGY ORGANIC CHEMISTRY STEROIDS
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creator	CAVEZZA ALEXANDRE RADISSON XAVIER PICHAUD PATRICK
description	Production of 7beta-hydroxy-dehydroepiandrosterone (I), comprises: (1) protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone (II) using an optionally O-protected hydrazine; (2) reduction of the 7-keto group of the obtained 17-oxime (IV) using alkali metal borohydride; (3) deprotecting the oxime; and (4) deprotecting the obtained 3-O-acetyl compound (V) by transesterification. Production of 7beta-hydroxy-dehydroepiandrosterone of formula (I) comprises: (1) regioselective protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone of formula (II) using a hydrazine compound of formula NH2OR (III) in non-complexed form; (2) chemoselective and diastereoselective reduction of the 7-keto group of the obtained 3-O-acetyl-7-oxo-dehydroepiandrosterone 17-oxime of formula (IV) using alkali metal borohydride as reducing agent; (3) deprotecting the oxime; and (4) deprotecting the obtained 3-O-acetyl-7beta-hydroxy-dehydroepiandrosterone of formula (V) by transesterification. R = H, 1-3C alkyl, butyl, tert. butyl (optionally substituted benzyl (specifically 2-chlorobenzyl)), CH2SPh, SiMe3 or SiMe2tBu. L'invention se rapporte à un nouveau procédé de préparation de la 7béta-hydroxydéhydroépiandrostérone de formule (1) :
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Production of 7beta-hydroxy-dehydroepiandrosterone of formula (I) comprises: (1) regioselective protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone of formula (II) using a hydrazine compound of formula NH2OR (III) in non-complexed form; (2) chemoselective and diastereoselective reduction of the 7-keto group of the obtained 3-O-acetyl-7-oxo-dehydroepiandrosterone 17-oxime of formula (IV) using alkali metal borohydride as reducing agent; (3) deprotecting the oxime; and (4) deprotecting the obtained 3-O-acetyl-7beta-hydroxy-dehydroepiandrosterone of formula (V) by transesterification. R = H, 1-3C alkyl, butyl, tert. butyl (optionally substituted benzyl (specifically 2-chlorobenzyl)), CH2SPh, SiMe3 or SiMe2tBu. L'invention se rapporte à un nouveau procédé de préparation de la 7béta-hydroxydéhydroépiandrostérone de formule (1) :</description><edition>7</edition><language>eng ; fre</language><subject>CHEMISTRY ; METALLURGY ; ORGANIC CHEMISTRY ; STEROIDS</subject><creationdate>2003</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20030815&DB=EPODOC&CC=FR&NR=2835839A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76290</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20030815&DB=EPODOC&CC=FR&NR=2835839A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>CAVEZZA ALEXANDRE</creatorcontrib><creatorcontrib>RADISSON XAVIER</creatorcontrib><creatorcontrib>PICHAUD PATRICK</creatorcontrib><title>Production of 7 beta-hydroxy-dehydroepiandrosterone, comprises, e.g. selective oximation and reduction process involving 3-O-acetyl-7-oxo-dehydroepiandrosterone</title><description>Production of 7beta-hydroxy-dehydroepiandrosterone (I), comprises: (1) protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone (II) using an optionally O-protected hydrazine; (2) reduction of the 7-keto group of the obtained 17-oxime (IV) using alkali metal borohydride; (3) deprotecting the oxime; and (4) deprotecting the obtained 3-O-acetyl compound (V) by transesterification. Production of 7beta-hydroxy-dehydroepiandrosterone of formula (I) comprises: (1) regioselective protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone of formula (II) using a hydrazine compound of formula NH2OR (III) in non-complexed form; (2) chemoselective and diastereoselective reduction of the 7-keto group of the obtained 3-O-acetyl-7-oxo-dehydroepiandrosterone 17-oxime of formula (IV) using alkali metal borohydride as reducing agent; (3) deprotecting the oxime; and (4) deprotecting the obtained 3-O-acetyl-7beta-hydroxy-dehydroepiandrosterone of formula (V) by transesterification. R = H, 1-3C alkyl, butyl, tert. butyl (optionally substituted benzyl (specifically 2-chlorobenzyl)), CH2SPh, SiMe3 or SiMe2tBu. 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Production of 7beta-hydroxy-dehydroepiandrosterone of formula (I) comprises: (1) regioselective protection of the 17-keto group of 3-O-acetyl-7-oxo-dehydroepiandrosterone of formula (II) using a hydrazine compound of formula NH2OR (III) in non-complexed form; (2) chemoselective and diastereoselective reduction of the 7-keto group of the obtained 3-O-acetyl-7-oxo-dehydroepiandrosterone 17-oxime of formula (IV) using alkali metal borohydride as reducing agent; (3) deprotecting the oxime; and (4) deprotecting the obtained 3-O-acetyl-7beta-hydroxy-dehydroepiandrosterone of formula (V) by transesterification. R = H, 1-3C alkyl, butyl, tert. butyl (optionally substituted benzyl (specifically 2-chlorobenzyl)), CH2SPh, SiMe3 or SiMe2tBu. L'invention se rapporte à un nouveau procédé de préparation de la 7béta-hydroxydéhydroépiandrostérone de formule (1) :</abstract><edition>7</edition><oa>free_for_read</oa></addata></record>
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subjects	CHEMISTRY METALLURGY ORGANIC CHEMISTRY STEROIDS
title	Production of 7 beta-hydroxy-dehydroepiandrosterone, comprises, e.g. selective oximation and reduction process involving 3-O-acetyl-7-oxo-dehydroepiandrosterone
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