Toluene → HCID 86673650, compound

Participants

Reaction Steps

Under N2, 1-benzoyl-(S)-5-biphenyl-4-ylmethyl-pyrrolidin-2-one (3a, R1=benzoyl) (1.34 g, 4 mmol) is dissolved in 4 mL toluene, and heated to reflux, sodium hydride (55% in mineral oil, 0.23 g, 5.2 mmol) is added, and stirred for 2 hours at reflux, then benzoyl chloride (0.62 g, 4.4 mmol) is added to the reaction mixture, the resulting mixture is then stirred for 2 hours at reflux. the reaction mixture is diluted with 5 mL saturated aqueous ammonium chloride solution and stirred for 15 min, stop stirring, and remove the lower aqueous layer. The organic phase is concentrated to dryness, the residue is purified by column chromatography (ethyl acetate/heptane=1/2) to yield (R/S)-1,3-Dibenzoyl-(S)-5-biphenyl-4-ylmethyl-pyrrolidin-2-one (4a, R1=benzoyl, R4=phenyl), the ratio of (3S,5S) to (3R,5S) is 30:70 as determined by HPLC. 1HNMR (400 MHz, CDCl3): 2.09 (m, 1H, 3-CHH), 2.34 (m, 1H, 3-CHH), 2.71 (d, 1H, 5-CHH), 2.96 (d, 1H, 5-CHH), 3.73 (m, 1H, 2-CH), 4.38 (m, 1H, 4-CH), 7.20˜8.10 (19H, m, aromatic).

Provenance & Evidence