Liquid chromatographic resolution of racemic amines and amino alcohols on a chiral stationary phase derived from crown ether

A chiral stationary phase (CSP) prepared by bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxyl acid to silica gel was successfully employed in resolving various racemic amines and amino alcohols including therapeutically active compounds such as amphetamine, phenylethanolamine, octopamine and norepinephrine. Related compounds such as cr-amino carbonyl compounds were also resolved on the CSP. In order to see the effect of organic and acidic modifiers in the mobile phase and the temperature of the column on the enantioselectivity exerted by the CSP, four racemic compounds which resolved well on the CSP were selected and their resolutions were investigated with the variation of organic and acidic modifiers in the mobile phase and the temperature of the column. From the results, the chromatographic factors such as capacity factors (k'), separation factors (alpha) and resolution factors (R(s)) were expected to be controlled to some extent by varying organic and acidic modifiers in the mobile phase and the temperature of the column. (C) 1999 Elsevier Science BN. All rights reserved.