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filingDate 2016-10-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5f51eddd5026b34ada1feb2c60ad9dc2
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publicationDate 2018-01-24-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-106516-A1
titleOfInvention PROCESS FOR THE PREPARATION OF 17b-HIDROXI-DES-A-ANDROST-9,10-EN-5-ONA
abstract Process for the synthesis of 17b-hydroxy-des-A-androst-9,10-en-5-one, the compound of formula (1), which can be used as an intermediate in the synthesis of retroprogesterone. Claim 1: Process for the synthesis of 17b-hydroxy-des-A-androst-9,10-en-5-one, compound of formula (1), comprising the following steps: a) reaction of the compound (4eR, 6eS , 9eS, 9bS) -decaidro-6a-methyl-cyclopenta [f] [1] benzopyran-3,7-dione, compound of formula (2), with bromide or ethylmagnesium chloride to give the mixture of isomers (4S, 5R , 7aS) -5-hydroxy-7a-methyl-4- (3-isopentyl) octahydro-1H-inden-1-one and (4S, 5S, 7aS) -5-hydroxy-7a-methyl-4- (3- isopentyl) octahydro-1H-inden-1-one, intermediate mixture of formula (3); b) oxidation of the intermediate mixture of formula (3) to give (4S, 7aS) -7a-methyl-4- (3-isopentyl) hexahydro-1H-inden-1,5 (4H) -dione, intermediate of formula ( 4); c) cyclization of the intermediate of formula (4) to give des-A-androst-9,10-en-5,17-dione, intermediate of formula (5); d) reduction of the intermediate of formula (5) to 17b-hydroxy-des-A-androst-9,10-en-5-one, compound of formula (1). Claim 10: Mixture of formula (3) of the isomers of (4S, 5R, 7aS) -5-hydroxy-7a-methyl-4- (3-isopentyl) octahydro-1H-inden-1-one of formula (6) and (4S, 5S, 7aS) -5-hydroxy-7a-methyl-4- (3-isopentyl) octahydro-1H-inden-1-one of formula (7).
priorityDate 2015-10-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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