Methyl Benzoate → HCID 131733077, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (150 mg, 55% in mineral oil, 3.75 mmol) in toluene (1 mL) is added (5S)-biphenyl-4-ylmethyl-1-(4-methoxybenzyl)pyrrolidin-2-one (3a, R1=p-methoxybenzyl) (694 mg, 1.86 mmol) followed by addition of benzoic acid methyl ester (253 mg, 1.86 mmol), the resulting mixture is then heated at 130° C. for 9 h. After cooling to room temperature, NH4Cl (sat. aq, 5 mL) is added followed by ethyl acetate (3 mL). The organic layer is separated, washed with brine and concentrated to give (3R/S)-benzoyl-(5S)-biphenyl-4-ylmethyl-1-(4-methoxybenzyl)pyrrolidin-2-one (4a, R1=p-methoxybenzyl, R4=phenyl) as a mixture of (3S,5R) and (3R,5R) diastereomers (50:40 as determined by HPLC). 1HNMR (400 MHz, DMSO): 1.82-2.08 (m, 2H), 2.25-2.70 (m, 2H), 3.00-3.26 (m, 2H), 3.73 (s, 3H), 4.00-4.10 (m, 1H), 4.20-4.52 (m, 1H), 4.94-5.09 (m, 1H), 6.86˜8.10 (18H, m, aromatic). MS (ESI, m/e) 476 (MH+).

Provenance & Evidence