Boron tribromide → HCID 21480575, compound

Participants

Reaction Steps

3,4,4a,5,6,7,8,8a,-Octahydro-3-hydroxymethyl-6-((4-methoxyphenyl)methyl)-quinolin-2[1H]-one (0.26 g) (prepared according to Example 7) was dissolved in dichloromethane and cooled to ice temperature. 1M Boron tribromide in dichloromethane (4.3 ml) was added and the mixture was left 2 hours after which a further 75 ml of dichloromethane was added. After a further 1 hour the reaction mixture was quenched by addition of water (2 ml) and evaporated under reduced pressure. The residue was dissolved in methanol (100 ml) containing conc. HCl (1 ml) and the methanol was evaporated under reduced pressure; the process being repeated three time. The residue was basified with saturated sodium bicarbonate solutions and was extracted into chloform. The chloroform layer was dried (MgSO4) and evaporated. The residue was recrystallised from isopropanol/diisopropyl ether to give the title compound (0.035 g) mp 126°-128° C.

Provenance & Evidence