Tetrahydrofuran → (S)-N-benzyloxycarbonyl-3-carbamoyloxycarbonyl-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

To (S)-N-benzyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline(1 g) in tetrahydrofuran (5 mL) was added carbonyl diimidazole (0.6 g) and stirred for 45 minutes. Ammonium hydroxide (30%, 5 mL) was added and after overnight stirring, the reaction mixture was extracted with ethyl acetate. The extract was washed with water, 0.5 N HCl, concentrated and recrystallized from ethanol to yield the product as a white solid (0.67 g). Melting point 136.0-137.9° C.

Provenance & Evidence