Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate

The synthesis, stereostructure, and enantiomeric separation by chromatography of a new, chiral anxiolytic agent, deramciclane fumarate (2,(−)-[1R,2S,4R]-2-(2-dimethylaminoethoxy)-2-phenyl-1,7,7-trimethylbicyclo[2.2.1]heptane fumarate, EGIS-3886), is described. The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X-ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 × 4.6 mm; 10 μm) and hexane-ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99.9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed. Chirality 11:689–693, 1999. © 1999 Wiley-Liss, Inc.