Benzyl Bromide → HCID 10745912, compound

Participants

Reaction Steps

A solution of (1R,3S)-benzyl 2-acetyl-1-(1-adamantyl)methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (6.3 g, 12.7 mmol) in dry DMF (50 ml) was added dropwise to a slurry of sodium hydride (60% dispersion in oil/0.56 g, 14 mmol) in dry DMF (20 ml) under nitrogen at room temperature. The reaction mixture was stirred for 15 minutes at room temperature to which was added dropwise a solution of benzyl bromide (1.6 ml, 13.5 mmol) in DMF (10 ml). The reaction was stirred for a further one hour, diluted with ethyl acetate (150 ml), washed successively with 2N HCl (150 ml), brine (3×150 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the product as a yellow foam which was used without further purification. (7.45 g, 100%).

Provenance & Evidence