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US 10,189,765 B2Granted
Process for the preparation of 17β-hydroxy-des-A-androst-9,10-en-5-one
AssigneeIndustriale Chimica S.R.L.
InventorsRoberto Lenna, Roberto Di Brisco
Life of this patent
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Abstract
The present invention relates to a new process for the synthesis of 17β-hydroxy-des-A-androst-9,10-en-5-one, the compound of the following formula (1), which can be used as an intermediate in the synthesis of retroprogesterones.
Claims10
A process for the synthesis of 17β-hydroxy-des-A-androst-9,10-en-5-one, compound (1), comprising the following steps:
- a) reaction of compound (4aR,6aS,9aS,9bS)-decahydro-6a-methyl-cyclopenta[f][1]benzopyran-3,7-dione, compound (II), with ethylmagnesium bromide or ethylmagnesium chloride to give the mixture of isomers (4S,5R,7aS)-5-hydroxy-7a-methyl-4-(3-oxopentyl)octahydro-1H-inden-1-one and (4S,5S,7aS)-5-hydroxy-7a-methyl-4-(3-oxopentyl)octahydro-1H-inden-1-one, intermediate mixture (III):
- b) oxidation of the intermediate mixture (III) to give (4S,7aS)-7a-methyl-4-(3-oxopentyl)hexahydro-1H-inden-1,5(4H)-dione, intermediate (IV):
- c) cyclization of the intermediate (IV) to give des-A-androst-9,10-en-5,17-dione, intermediate (V):
- d) reduction of the intermediate (V) to 17β-hydroxy-des-A-androst-9,10-en-5-one, compound (1):
1 more element
A mixture (III) of the isomers (4S,5R,7aS)-5-hydroxy-7a-methyl-4-(3-oxopentyl)octahydro-1H-inden-1-one and (4S,5S,7aS)-5-hydroxy-7a-methyl-4-(3-oxopentyl)octahydro-1H-inden-1-one:
Dependencies are inferred from the claim text.