SYNTHESIS OF OPTICALLY-ACTIVE CIS-N-BENZYL-2-(HYDROXYMETHYL)CYCLOHEXYLAMINE AND RESOLUTION OF CARBOXYLIC-ACIDS

A new basic optical resolving reagent is proposed. Optically active cis-N-benzyl-2-(hydroxy-methyl)cyclohexylamine [2] was obtained by reduction of optically active cis-2-(benzamido)cy-clohexanecarboxylic acid [1] which was prepared by preferential crystallization of its benzyl-amine salt. A number of racemic carboxylic acids, such as (±)-malic acid [3], (±)-α-methoxyphenyl-acetic acid [4], (±)-α-phenyIpropionic acid (5], (±)-trans-2-phenylcyclohexanecarboxylic acid [6] (±)-trans-l,2-cyclohexanedicarboxylic acid [7], and (±)-α-ureido-α-(2-thienyl) acetic acid (8 ] have been resolved by fractional crystallization of their diastereomeric salts with [2]. © 1979, The Chemical Society of Japan. All rights reserved.