Benzyl Bromide → tert-butyl 5-benzyloctahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Participants

Reaction Steps

To a solution of 2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (1.0 g, 4.2 mmol) in acetonitrile (20 mL) was added benzyl bromide and the mixture heated at reflux for 2.5 h. The reaction mixture was concentrated in vacuo and the resultant black oil was dissolved in MeOH (50 mL). To this solution was slowly added sodium borohydride (1.2 g, 32.0 mmol) over 10 min, then the mixture was heated at reflux for 2.5 h. After cooling to RT, the reaction mixture was concentrated in vacuo before EtOAc and an aqueous saturated solution of ammonium chloride were added. The reaction mixture was stirred at RT for 1 h. The organic layer was isolated, dried (Na2SO4) and concentrated in vacuo to give the title compound as a cream solid (0.78 g, 59%).

Provenance & Evidence