[(S)-1-(7-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid benzyl ester → (S)-1-(7-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamine

Participants

Reaction Steps

A mixture of [(S)-1-(7-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid benzyl ester (1.5 g, 3.89 mmol) and 10% Pd/C (150 mg) in IMS (25 mL) was degassed with a stream of nitrogen and, after addition of HCl (1M, 2.5 mL), was stirred at RT (room temperature) under a hydrogen atmosphere for 5.5 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The resulting residue was partitioned between DCM (dichloromethane) and water, the organic layer was then washed with a saturated solution of NaHCO3, dried (Na2SO4) and concentrated in vacuo affording (S)-1-(7-Methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine as a brown solid (1.41 g, 96%). LCMS: RT 2.07 min [M−NH2]1 235.1

Provenance & Evidence