Research Article: (1R,3R,3aS,8aR)-4-Oxo-3-phenyl-1-[(1R)-1-phenyl­eth­yl]deca­hydro­cyclo­hepta­[b]pyrrol-1-ium bromide

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Victor B. Rybakov, Dmitry S. Belov, Evgeny R. Lukyanenko, Alexander V. Kurkin, Marina A. Yurovskaya.


The title chiral compound, C23H28NO+·Br−, was obtained from an optically active amino­ethanol precursor. The pyrrolidine heterocycle has an envelope conformation, with the C atom α-positioned with respect to the keto group deviating by 0.570 (6) Å from the mean plane of other atoms. The trans-fused seven-membered ring adopts a pseudo-chair conformation. The two phenyl rings form a dihedral angle of 85.1 (2)°. The cationic center and the bromide anion are connected through an N—H⋯Br hydrogen bond.

Partial Text

For general background to the aza-Cope–Mannich sequence, see: Overman (1992 ▶, 2009 ▶). For natural products with cyclo­hepta­[b]pyrrolidine, see: Earley et al. (2005 ▶); Martin et al. (2008 ▶). For biologically active compounds, see: Tamiz et al. (2000 ▶). For the preparation of cis-cyclo­hepta­[b]pyrrolidines, see: Belov et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).




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