INTERMEDIATES FOR SYNTHESIS OF VITAMIN D

The invention relates to an improved process for preparing [(3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7 a- methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminu m hydride and hexamethylphosphoric triaminde in the presence of a c...

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1. Verfasser:	DANIEWSKI, ANDRZEJ ROBERT
Format:	Patent
Sprache:	eng ; fre
Schlagworte:	ACYCLIC OR CARBOCYCLIC COMPOUNDS APPARATUS THEREFOR CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY CHEMISTRY GENERAL METHODS OF ORGANIC CHEMISTRY METALLURGY ORGANIC CHEMISTRY PERFORMING OPERATIONS PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL THEIR RELEVANT APPARATUS TRANSPORTING
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creator	DANIEWSKI, ANDRZEJ ROBERT
description	The invention relates to an improved process for preparing [(3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7 a- methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminu m hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R-Cu, wherein R is (see formula I) and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C 1- 4 alkyl group, benzyl, or benzyl substituted by at least one C1-4 alkyl groups to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione.
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(S)-(+)-2,3,7,7a-tetrahydro-7 a- methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminu m hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R-Cu, wherein R is (see formula I) and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C 1- 4 alkyl group, benzyl, or benzyl substituted by at least one C1-4 alkyl groups to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione.</description><language>eng ; fre</language><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS ; APPARATUS THEREFOR ; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY ; CHEMISTRY ; GENERAL METHODS OF ORGANIC CHEMISTRY ; METALLURGY ; ORGANIC CHEMISTRY ; PERFORMING OPERATIONS ; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL ; THEIR RELEVANT APPARATUS ; TRANSPORTING</subject><creationdate>2009</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=20090113&DB=EPODOC&CC=CA&NR=2298944C$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,778,883,25547,76298</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20090113&DB=EPODOC&CC=CA&NR=2298944C$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>DANIEWSKI, ANDRZEJ ROBERT</creatorcontrib><title>INTERMEDIATES FOR SYNTHESIS OF VITAMIN D</title><description>The invention relates to an improved process for preparing [(3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7 a- methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminu m hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R-Cu, wherein R is (see formula I) and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C 1- 4 alkyl group, benzyl, or benzyl substituted by at least one C1-4 alkyl groups to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione.</description><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS</subject><subject>APPARATUS THEREFOR</subject><subject>CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY</subject><subject>CHEMISTRY</subject><subject>GENERAL METHODS OF ORGANIC CHEMISTRY</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><subject>PERFORMING OPERATIONS</subject><subject>PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL</subject><subject>THEIR RELEVANT APPARATUS</subject><subject>TRANSPORTING</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2009</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZNDw9AtxDfJ1dfF0DHENVnDzD1IIjvQL8XAN9gxW8HdTCPMMcfT19FNw4WFgTUvMKU7lhdLcDPJuriHOHrqpBfnxqcUFicmpeakl8c6ORkaWFpYmJs7GhFUAAIe_I1E</recordid><startdate>20090113</startdate><enddate>20090113</enddate><creator>DANIEWSKI, ANDRZEJ ROBERT</creator><scope>EVB</scope></search><sort><creationdate>20090113</creationdate><title>INTERMEDIATES FOR SYNTHESIS OF VITAMIN D</title><author>DANIEWSKI, ANDRZEJ ROBERT</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_CA2298944C3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; fre</language><creationdate>2009</creationdate><topic>ACYCLIC OR CARBOCYCLIC COMPOUNDS</topic><topic>APPARATUS THEREFOR</topic><topic>CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY</topic><topic>CHEMISTRY</topic><topic>GENERAL METHODS OF ORGANIC CHEMISTRY</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><topic>PERFORMING OPERATIONS</topic><topic>PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL</topic><topic>THEIR RELEVANT APPARATUS</topic><topic>TRANSPORTING</topic><toplevel>online_resources</toplevel><creatorcontrib>DANIEWSKI, ANDRZEJ ROBERT</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>DANIEWSKI, ANDRZEJ ROBERT</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>INTERMEDIATES FOR SYNTHESIS OF VITAMIN D</title><date>2009-01-13</date><risdate>2009</risdate><abstract>The invention relates to an improved process for preparing [(3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione]. (S)-(+)-2,3,7,7a-tetrahydro-7 a- methyl-1H-indene-1,5(6H)-dione is reduced by reaction with diisobutylaluminu m hydride and hexamethylphosphoric triaminde in the presence of a catalyst of the formula R-Cu, wherein R is (see formula I) and R1, R2 and R3 are each, independently, selected from the group consisting of C1-7 alkyl, phenyl, phenyl substituted by at least one C 1- 4 alkyl group, benzyl, or benzyl substituted by at least one C1-4 alkyl groups to form a reductate. The reductate is then treated with a bromine-containing electrophile to yield (3aR,4S,7aS)-4- bromooctahydro-7a-methyl-1H-indene-1,5-dione.</abstract><oa>free_for_read</oa></addata></record>
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subjects	ACYCLIC OR CARBOCYCLIC COMPOUNDS APPARATUS THEREFOR CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY CHEMISTRY GENERAL METHODS OF ORGANIC CHEMISTRY METALLURGY ORGANIC CHEMISTRY PERFORMING OPERATIONS PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL THEIR RELEVANT APPARATUS TRANSPORTING
title	INTERMEDIATES FOR SYNTHESIS OF VITAMIN D
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