Synthesis and structure of N-(2-(1-adamantyl)-2-hydroxyethyl)cytisine diastereomers

Abstract

Diastereomers of N-(2-(1-adamantyl)-2-hydroxyethyl)cytisine were synthesized by reduction of N-(2-(1-adamantyl)-2-oxoethyl)cytisine with NaBH 4 . Their structures were established using x-ray structure analysis.

Synthesis and crystal structure of N(12)-(2-hydroxy-2-phenylethyl)cytisine

“…Comparison of the spectra showed that the chemical shifts for C-11 and C-13 in addition to the endo-and exo-protons of C-11 and C-13 were distributed differently for the (R)-2 and (S)-2 diastereomers [9]. In (R)-2, the resonance of H exo -11 (2.43 ppm) appeared at strong fields for exo-protons on C-11 and C-13.…”