The Resolution and Rotations of trans-2-Aminocyclohexanecarboxylic Acids and Derivatives

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Optically active trans-2-aminocyclohexanecarboxylic acids [(+)-1 and (−)-1] have been prepared by a preferential crystallization of racemic N-benzoyl trans-2-aminocyclohexanecarboxylic acid [(±)-2]. Active 2 have been used for preparation of such active trans-1,2-disubstituted cyclohexanes as (+)-, and (−)-ethyl trans-2-aminocyclohexanecarboxylate [(+)-3 and (−)-3], (+)-, and (−)-trans-2-aminocyclohexanemethanol [(+)-4 and (−)-4], (+)-trans-2-bromomethylcyclo-hexylamine hydrobromide [(+)-5], and (+)-trans-2-methylcyclohexylamine [(+)-6]. Amine-nitrous acid reaction of these cyclohexylamines to give the corresponding hydroxy compounds (7, 8, 9) has also been examined. It was confirmed that the signs of optical rotations of these hydroxy compounds are the same as those of the starting amines. It has been shown that observed molecular rotations of these active 1,2-disubstituted cyclohexanes are in agreement, in sign and order of magnitude, with those calculated following Brewster's procedures presented in 1959 and in 1967.
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