Process for resolution of optical isomers

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

1988-03-30

1989-07-18

Warren, Charles F.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544134, 546273, 546288, 546274, 546153, 564 56, 548484, 549 57, 560 27, 560251, 558417, C07C12717, C07D20904, C07D41700, C07D40100

Patent

active

048495271

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]propox y]benzonitrile into its individual enantiomers is described. The process comprises converting the racemic modification into a pair of diastereomeric urea derivativesby 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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