Water → HCID 22626865, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis (triphenylphosphine)palladium (0) (4.10 g, 0.0035 mol) was added to a suspension of N-tert-butyloxycarbonyl-4,4-dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline (36.37 g, 0.089 mol) and zinc cyanide (10.44 g, 0.089 mol) in anhydrous dimethyl formamide (280 ml) under argon. The resultant was heated at 100° C. for 4 hours, cooled and poured into water (800 ml). The mixture was filtered through kieselguhr and the filter cake washed with ethyl acetate. The bilayered filtrate was separated and the aqueous layer extracted into ethyl acetate (4×500 ml). Combined organics were washed with water (3×250 ml), brine (250 ml), dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel using 0-15 % ethyl acetate in hexane gradient elution to afford the title compound as a colourless oil (21.75 g, 85%).

Provenance & Evidence