New Enantiomerically Pure Aminoalcohols from (R)-a- Methylbenzylamine and Cyclohexene Oxide

The new chiral aminoalcohois N-{(S)-[cyclohexan-(S)-2-ol] }-(R)-ct-methylbenzyl amine 1 and N-{(R)-[cyciohexan-(R)-2-ol]}-(R)-a-methylbenzyl amine 2 were prepared by reaction of (R)-ct-methylbenzylamine with cyclohexene oxide at 160 °C. The diastereoisomers were separated by fractional crystallization of the corresponding ammonium chlorides N-{(S)- [cyclohexan-(S)-2-ol]}-(R)-tx-methylbenzyl ammonium chloride I-HCI and N-{(R)-[cyclohexan- (R)-2-oi]}-(R)-ct-methylbenzyl ammonium chloride 2-HCI. The absolute configuration of all stereocenters in 1.HC1 and 2.HCI was determined by X-ray diffraction analyses