1-{(1<i>S</i>,2<i>S</i>,4<i>R</i>)-7,7-Dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo [2.2.1]heptan-2-yl}-1<i>H</i>-benzo[<i>d</i>]imidazole

Abstract

A three-step synthesis of 1-{(1S,2S,4R)-7,7-dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo[2.2.1]heptan-2-yl}-1H-benzo[d]imidazole, prepared from camphor derived diamine, is disclosed. The absolute configuration at the chiral center bearing benzo[d]imidazole moiety was confirmed by NOESY. The structure of a newly synthesized compound was confirmed by 1H- and 13C-NMR, 2D NMR, IR spectroscopy, and high resolution mass-spectrometry.

Keywords

• camphor
• bifunctional noncovalent organocatalysts
• benzo[<i>d</i>]imidazole
• Michael addition
• 2-fluoronitrobenzene
• nucleophilic aromatic substitution