Benzyl Alcohol → HCID 53979657, compound

Participants

Reaction Conditions

Reaction Steps

To a solution stirred under argon at room temperature of methyl (±)-8-carboxy-2-methyl-3-oxo-2,3,4,5-tetrahydro-2-benzazepine-4-acetate (0.30 g, 1 mmol) and triethylamine (0.16 mL, 1.2 mmol) in toluene was added diphenylphosphorylazide (0.31 g, 1.2 mmol). The resulting mixture was heated at 80° C. for 1 h, then was allowed to cool, and benzyl alcohol (0.22 g, 2 mmol) was added. The mixture was heated at 80° C. for 4 h, then was concentrated to remove the toluene. The residue was dissolved in EtOAc, and the solution was washed sequentially with 5% aqueous NaHCO3, 1N HCl, and brine. Drying (MgSO4), concentration, and chromatography (silica gel, 1% MeOH/CH2Cl2) gave the title compound as a colorless solid (0.20 g, 47%): 1H NMR (CDCl3) δ7.40-7.30 (m, 6H), 7.06 (dd, J=8.3, 2 Hz, 1H), 7.02 (d, J=8.3 Hz, 1H), 6.65 (br s, 1H), 5.28 (d, J=16.7 Hz, 1H), 5.20 (s, 2H), 3.80 (m, 1H), 3.79 (d, J=16.7 Hz, 1H), 3.70(s, 3H), 3.03 (s, 3H), 3.00 (m, 2H), 2.88 (m, 1H), 2.41 (dd, J=16.8, 5.3, 1H).

Provenance & Evidence