Benzylamine → tert-butyl (3aR,7aS)-2-(benzylamino)-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of intermediate 76 (200 mg, 0.0.740 mmol), benzylamine (0.5 mL, 4.6 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 207 mg of the product 189. 1H NMR (CDCl3) δ 8.56 (s, 1 H), 7.50-7.20 (m, 5 H), 5.15-4.95 (m, 2 H), 4.35-4.05 (m, 2 H), 2.85-2.55 (m, 1 H), 2.25-2.05 (m, 1 H), 1.90-1.05 (m, 15 H); MS: m/z 330 (M++1).

Provenance & Evidence