Sodium Cyanide → tert-Butyl-7-(cyanomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Steps

To a solution of 21.76 mmol of tert-butyl-7-(bromomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 80 ml DMF were added at 0° C. 65.3 mmol sodium cyanide in small portions. The mixture was stirred at room temperature for 2 h. Brine solution was added to the mixture and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and filtered. Evaporation of the solvent gave 5.6 g of a brown oil. The material was purified by flash chromatography to yield 1.63 g of a pale yellow solid (27.5%).

Provenance & Evidence