Benzyl Bromide → HCID 57189772, compound

Participants

Reaction Steps

A solution of benzylbromide (0.44 ml, 0.0037 mol) in toluene (5 ml) was added dropwise to the refluxing mixture of (-)-(4aS,6S,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-((4-methoxyphenyl)methyl)quinolin-2(1H)-one (0.512 g, 0.0019 mol, prepared according to Example 32), powdered NaOH (0.175 g), potassium carbonate (0.35 g), tetraammonium hydrogen sulphate (0.02 g) and toluene (20 ml). The reaction was refluxed for 4 days. The reaction mixture was then cooled, diluted with toluene and then washed with water. It was then dried over sodium sulphate, filtered and the solvent evaporated. The solid was then chromatographed on a silica gel column in ethylacetate. The first fraction was collected, the solvent evaporated and the resulting solid recrystallised from acetonitrile to give the title compound (0.15 g), mp=118-9° C.; [α]D25 =-10° (1%, CHCl3).

Provenance & Evidence