STRUCTURAL AND CONFORMATIONAL STUDY OF SOME N'-P-HALOBENZOYL DERIVATIVES OF THE 3-BETA-AMINO-3-ALPHA-METHOXYCARBONYL(OR CYANO)-N8-SUBSTITUTED NORTROPANES

A series of N'-p-F(or Cl)-benzoyl derivatives of 3-beta-amino-3-alpha-methoxycarbonyl(or cyano)-N8-substituted nortropanes has been synthesized and studied by IR, H-1 and C-13 NMR spectroscopy, and the crystal structure of 3-alpha-methoxycarbonyl-3-beta-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 Vlb in the crystalline state.