Chiral high-performance liquid chromatography of some related bicyclic lactams

Chromatographic methods utilising a Chiralcel OC cellulose-based column were developed for the chiral resolution of optical isomers of the cognition-enhancing ISF 4185 and related bicyclic lactams. These methods were scaled up for the preparation of purified samples of enantiomers, one pair of which was submitted to X-ray analysis. The resolution of the enantiomers derived from these compounds appears to be mainly dependent on their ability to hydrogen bond to the chiral stationary phase.