Structural and spectroscopic study of condensed piperidine bicyclanols. 3-Phenethyl-3-azabicyclo[3.2.1]octan-8-α-ol

Abstract

The IR and 1H and 13C NMR spectra of 3-phenethyl-3-azabicyclo[3.2.1]octan-8-α-ol have been studied in several media, and its crystal structure has been determined by X-ray diffraction. The bicyclic system adopts a chair-envelope conformation with both OH and phenethyl groups in equatorial positions with respect to the piperidine ring. The existence of OH⋯N intermolecular hydrogen bonding in the solid state has been revealed by X-ray and IR data. The results obtained are compared with those previously found for the corresponding β-epimer. © 1989.