tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-Butyl 7-(aminomethyl)-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Steps

tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate (169 mg, 0.434 mmol) was dissolved in methanol (15 mL) under an atmosphere of nitrogen. Raney nickel (100 mg) was added and the reaction mixture stirred at room temperature under an atmosphere of hydrogen for 9 hours. The catalyst was removed by filtration. The filtrate was concentrated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 103 mg (0.262 mmol, 60%).

Provenance & Evidence