ChemInform Abstract: Structural and Conformational Study of Some N′-p-Halobenzoyl Derivatives of the 3β-Amino-3α-methoxycarbonyl(or cyano)-N8- Substituted Nortropanes.

Abstract

Abstract A series of N ′- p -F(or Cl)-benzoyl derivatives of 3β-amino-3α-methoxycarbonyl(or cyano)- N 8-substituted nortropanes has been synthesized and studied by IR, 1 H and 13 C NMR spectroscopy, and the crystal structure of 3α-methoxycarbonyl-3β- p -chlorobenzamido-tropane ( VIb ) has been determined by X-ray diffraction. The compounds studied display, in deuterochloroform, a chair envelope conformation very flattened at C3 and puckered at N8, with the benzamido and methoxycarbonyl groups in pseudo-equatorial and pseudo-axial positions respectively. In this solvent, intramolecular hydrogen bondings are observed. As regards the bicyclic system, results are in close agreement with those found for compound VIb in the crystalline state.