Process for resolution of optical isomers

Details Process for resolution of optical isomers Process for resolution of optical isomers

1982-09-13

1984-07-31

Bond, Robert T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546141, 546153, 546193, 546201, 546202, 546205, 546210, 546288, 548465, 548472, 548135, 548136, 548523, 548527, 548525, 548517, 548541, 548550, 548478, 549 57, 549 63, 549469, 549480, 544153, 544147, 544129, 544124, 544141, 544128, 544145, 544144, 564303, 544146, 564308, 544134, C07D40112

Patent

active

044631766

ABSTRACT:
A process for resolving a racemic modification of .beta.-adrenergic aryl- or hetaryl-oxypropanolamines such as (.+-.)-2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy] benzonitrile into its individual enantiomers is described. The process comprises converting the racemic modification into a pair of diastereomeric urea derivatives by reaction with a chiral aralkylisocyanate; separation into the individual diastereomers; and facile regeneration of the starting amine by cleavage of the intermediate urea compound using hydrazine. This final step is improved by the addition of an .alpha.-keto carboxylic acid, such as pyruvic acid, which functions as a scavenger of nucleophilic by-products.

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