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Synthesis and structural and conformational study of 3α-methoxycarbonyl-3β-(3′,4′,5′-trimethoxyb enzamido)-N8-substituted nortropanes

AuthorsBurgos, C.; Gálvez, E.; Sanz-Aparicio, J. ; Fonseca, I.; Bellanato, Juana
Issue Date1992
CitationJournal of Molecular Structure 267: 79-86 (1992)
AbstractTwo 3α-methoxycarbonyl-3β-(3′,4′,5′-trimethoxyb enzamido)-N8-substituted nortropanes have been synthesized and studied by IR, 1H and 13C NMR spectroscopy and the crystal structure of 3α-methoxycarbonyl-3β-(3′,4′,5′,-trimethoxy benzamido) tropane (IIa) has been determined by X-ray diffraction. The compounds studied display in deuterochloroform the same preferred conformation. The pyrrolidine and piperidine rings adopt a flattened N8 envelope and distorted chair conformation, puckered at N8 and markedly flattened at C3, with the N-substituent in equatorial position. This conformation seems to be governed by an intramolecular hydrogen bond. The crystal structure of IIa shows a complex hydrogen bonding network. Concerning the tropane skeleton, the X-ray results for IIa are quite similar to those found for compounds IIa,b in CDCl3 solution. Some spectroscopy data of the precursor amidonitriles are also described. © 1992.
Identifiersdoi: 10.1016/0022-2860(92)87013-L
issn: 0022-2860
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