High-performance liquid chromatographic enantioseparation of bicyclic 1,3-amino alcohols

Different high-performance liquid chromatographic methods were developed for the separation and identification of enantiomers of diendo- and diexo-3-aminobicyclo[2.2.1]heptane-2-methanol and diendo- and diexo-3-amino-bicyclo[2.2.1]hept-5-ene-2-methanol derivatives. Direct separation was carried out on a naphthylethyl carbamate-derivatized beta-cyclodextrin (Cyclobond I 2000 SN) stationary phase, which was used in the polar-organic mode. This allowed the simultaneous separation of stereoisomers of alcohol and ester analogs of the bicyclic 1,3-amino alcohols. Alternatively, the derivatization of amino alcohols on the amino group with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide produced diastereomers which were separable with high resolution (Rs>5-10) on a LiChrospher RP-18 stationary phase. The order of elution of the enantiomers was determined by both direct and indirect methods.