Boron tribromide → 6-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Participants

Reaction Steps

To a solution of the title A compound of Example 1 (3.8 g, 21.5 mmol; 3,4-dihydro-6-methoxy-2-[2-(4-phenyl-1-piperidinyl)-ethyl]-1(2H)-isoquinolinone, monohydrochloride) in methylene chloride (50 mL) at −78° C. was added a solution of boron tribromide (1M, 53.7 mL, 53.7 mmol) under nitrogen. The reaction mixture was stirred at for 16 hours, quenched with saturated amminium chloride solution and extracted repeatedly with EtOAc. The organic layer was dried over MgSO4 and concentrated to give the crude product which was triturated with acetone to afford the title compound (2.3 g, 66% yield) as an off-white solid.

Provenance & Evidence