Boron tribromide → HCID 69823504, compound

Participants

Reaction Steps

A solution of 0.421 g (1:11 mmol) of trans-8-bromo-7,9-dimethoxy-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h] isoquinolin-6-one hydrochloride in 40 ml of methylene chloride was treated at −70° with 1.23 ml of a 1M BBr3 solution in methylene chloride. After 15 minutes the cooling bath was removed. After the solution had reached room temperature it was stirred for one hour, subsequently poured on to 80 ml of ice/sat. sodium hydrogen carbonate solution and extracted three times with 60 ml of methylene chloride. The organic phase was dried (Na2SO4), filtered and evaporated. Chromatography (silica gel, methylene chloride/methanol 9:1) yielded 0.315 g (83%) of trans-8-bromo-7-hydroxy-9-methoxy-2-methyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one, which was converted with HCl in methanol into the hydrochloride with m.p. 257-259°.

Provenance & Evidence