Preparation of S-(-)- and R-(+)-N-(quinuclidinyl-3)-amide
AssigneeChiron Laboratories A.S.
InventorGisle L. Johansen
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Abstract
Optical active forms of the carboxylic acid amines of 3-aminoquinuclidine of formula (I), and the preparation thereof. These can be hydrolysed to the optical active forms of 3-aminoquinuclidine.
Claims7
Process of preparing optically active stereo-isomeric forms of a racemic carboxylic acid amide of 3-aminoquinuclidine of the formula (I):
- ##STR3## wherein R means a straight or branched hydrocarbon chain of the general formula C.sub.n H.sub.(2n+1) wherein n is an integer 1 to 6, comprising the steps of
- preparing a racemic aminoamidechiral acid salt of the formula (II):
- ##STR4## wherein R is as defined above and HA is S-(+)-camphor-10-sulphonic acid or R-(-)-camphor-10-sulphonic acid by mixing a solution of said acid with a solution of the amide of formula (I);
- resolving the diastereomer salt in its optically active forms;
- and
- releasing the amide of formula (I) in the optically active form from the separated salt.
A process of preparing S-(-)-3-aminoquinuclidine or salts thereof, comprising hydrolyzing the enantiomer of absolute configuration 3-S of the formula (I):
- ##STR5##
A process of preparing R-(+)-3-aminoquinuclidine or salts thereof, comprising hydrolyzing the enantiomer of configuration 3-R of the formula (I):
- ##STR6##
Dependencies are inferred from the claim text.