Structural and conformational study of some N'-p-halobenzoyl derivatives of the 3β-amino-3α-methoxycarbonyl(or cyano)-N8-substituted nortropanes

Article abstract of DOI:10.1016/0022-2860(92)80010-F

A series of N'-p-F(or Cl)-benzoyl derivatives of 3β-amino-3α-methoxycarbonyl(or cyano)-N8-substituted nortropanes has been synthesized and studied by IR, 1H and 13C 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.