Process for stereospecific hydrolysis of piperidinedione derivatives
AssigneeSmithKline Beecham Corporation
InventorsAlan David Curzons, Lawson Willian Powell, Alan Martin Keay
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Abstract
A process for stereospecifically hydrolysing a mixture of the (+) and (−) isomers of a compound of formula (II), in which R is C1-6 alkyl; using a carboxyl esterase enzyme, (I) to form a compound of formula (IIIA), and thereafter separating the resulting compound of formula (IIIA) from the remaining (−) isomer of formula (II); or (ii) to form a compound of formula (IIIB) and thereafter separating the resulting compound of formula (IIIB) from the remaining (+) isomer of formula (II).
Claims12
A process for stereospecifically hydrolysing a mixture of the (+) and (−) isomers of a compound of formula (II):
- 5
- in which R is C1-6alkyl;
- using a carboxyl esterase enzyme,
- (i) to form a compound of formula (IIIA), 6
- and thereafter separating the resulting compound of formula (IIIA) from the remaining (−) isomer of formula (II);
- or
- ii) to form a compound of formula (IIIB):
- 7
- and thereafter separating the resulting compound of formula (IIIB) from the remaining (+) isomer of formula (II).
A process for subsequently converting a (−) compound of formula (III) directly to paroxetine by reducing the carboxylic acid group to a hydroxymethyl group and reducing the two keto groups in the piperidine ring and subsequently, converting the resulting piperidine carbinol to paroxetine or a pharmaceutically acceptable salt and/or solvate thereof.
A compound of formula (III) or a salt or hydrate thereof.
Dependencies are inferred from the claim text.