Method for producing 4,4-dimethyl-3β-hydroxypregna-8, 14-diene-21-carboxylic acid esters and intermediate products obtained by said method
AssigneeSchering Corporation
InventorsJens Geisler, Eric Winter
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Abstract
The invention relates to a method for representing compounds of the general formula (1). The invention further relates to the hitherto unknown compounds of general formulas (5, 6 and 7) in the form of intermediate products and to the use of 4,4-dimethyl-3β hydroxypregna-8,14-diene-21-carboxylic acid esters of the general formula (1) for producing 4,4-dimethyl-5α-cholesta-8,14,24-triene-3β-ol (2).
Claims7
A process for the production of 4,4-dimethyl-3β-hydroxypregna-8,14-diene-21-carboxylic acid esters of formula I
- in which R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl, by (a) dimethylating androstenedione 3
- (a) into 4,4-dimethylandrostenedione of formula 4
- (b) alkylating (4) into a 4,4-dimethyl-3-oxopregna-5,17-diene-21-carboxylic acid ester of formula 5
- in which
- R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl,
- (c) reducing (5) into a 4,4-dimethyl-3β-hydroxy-pregna-5,17-diene-21-carboxylic acid ester of formula 6
- in which
- R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl,
- (d) reducing the 17-double bond of (6) into a 4,4-dimethyl-3β-hydroxy-pregn-5-ene-21-carboxylic acid ester of formula 7
- in which
- R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl,
- and subsequently halogenating, dehydrohalogenating, isomerizing and converting into the 4,4-dimethyl-3β-hydroxypregna-8,14-diene-21-carboxylic acid ester of formula (1).
A 4,4-Dimethyl-3-oxopregna-5,17-diene-21-carboxylic acid ester of formula 5
- in which
- R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl.
A 4,4-Dimethyl-3β-hydroxy-pregna-5,17-diene-21-carboxylic acid ester of formula 6
- in which
- R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl.
A process for making an intermediate in the production of FF-MAS, comprising dimethylating androstenedione 3
- to produce a starting material a compound of formula 1
- in which R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl.
A process for making an intermediate in the production of FF-MAS, comprising alkylating a compound of formula 4
- into a compound of formula 5
- wherein R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl,
- and reducing the compound of formula (5) to a compound of formula (6)
A process for the production of an intermediate in the production of FF-MAS, comprising reducing a compound of formula (5),
- wherein R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl to a compound of formula (6)
A process for the production of an intermediate in the production of FF-MAS, comprising alkylating a compound of formula 4
- into a compound of formula 5
- wherein R1=hydrogen, branched or unbranched C1-C6 alkyl, phenyl, benzyl, ortho-, meta- or para-methylphenyl.
Dependencies are inferred from the claim text.