Boron tribromide → HCID 18367303, compound

Participants

Reaction Steps

A 1.0 M solution of boron tribromide in methylene chloride (2.08 ml) was added dropwise to a solution of 2-(4,5-diphenyl-2-oxazolyl)-1-(3-methoxybenzyl)piperidine (440 mg) in methylene chloride (2.5 ml) under ice cooling. The resulting mixture was stirred at the same temperature for 3 hours and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 2-(4,5-diphenyl-2-oxazolyl)-1-(3-hydroxybenzyl)piperidine (388 mg) as a pale yellow powder. FABMS (m/z): 410 (M+) mp: 204.7-208.3° C. IR (Film): 1600, 1585, 1255 cm-1NMR (CDCl3, δ): 1.2-1.95 (6H, m), 2.0-2.25 (1H, m), 3.05-3.11 (1H, m), 3.25-3.37 (1H, m), 3.73-3.81 (2H, m), 6.71-6.83 (3H, m), 7.13 (1H, q, J=7.7 Hz), 7.25-7.48 (11H, m)

Provenance & Evidence