NMR study of diastereoisomerism of 2-(1-aminoethyl)bicyclo[2.2.1]heptane and its hydrochloride (deitiforin) View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2001-06

AUTHORS

S. N. Tandura, A. N. Shumsky, E. F. Litvin, L. M. Kozlova, E. V. Shuvalova, V. Z. Sharf, S. P. Kolesnikov

ABSTRACT

The assignment of the signals for the H and C atoms of four diastereomers (without their separation) of 2-(1-aminoethyl)bicyclo[2.2.1]heptane (1) and its hydrochloride (2) (the antiviral drug deitiforin) was performed for the first time by two-dimensional 1H and 13C NMR spectroscopy. The effects of the substituent at position 2 of norbornane on the chemical shifts of the α-, β-, and γ-carbon atoms of the bicycle were examined using the increments for alkanes. The changes in the chemical shifts of the C(6) and C(7) atoms are substantially larger than those for the other C atoms, which made it possible to identify the exo and endo forms. Each of these forms exists as a mixture of two diastereomers. The effect of the positive charge of the N atom on the γ-protons, which are closely spaced, but separated by a number of covalent bonds, was considered on going from amine 1 to hydrochloride 2. Based on significant changes in shielding of these H atoms, the configurations of the asymmetric center in the CHMe(NH2) substituent of the diastereomers were established. More... »

PAGES

1014-1022

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1011313117695

DOI

http://dx.doi.org/10.1023/a:1011313117695

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1014636114


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