Toluene → HCID 86673650, compound

Participants

Reaction Steps

(S)-5-Biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (3a, R1=styryl) (50.0 g, 141.7 mmol) is heated to dissolve in 140 mL of anhydrous toluene under N2, add sodium hydride (8.04 g, 184.2 mmol) in portions, stir at this temperature for 10 min, then add methyl benzoate dropwise, reflux for 6 h, cool to room temperature, quench with saturated NH4Cl aqueous solution, separate the organic phase, extract with toluene (100 mL*3), the combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate under vacuum to obtain (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (4a, R1=styryl, R4=phenyl), the ratio of (3S,5S) to (3R,5S) is 70:30 as determine by HPLC. 1HNMR (400 MHz, CDCl3): 2.35 (m, 1H, 3-CHH), 3.26 (m, 3H, 5-CH2+3-CHH), 3.74 (m, 1H, 2-CH), 4.32 (m, 1H, 4-CH), 6.21 (m, 1H, C═CHH), 7.21˜7.80 (m, 20H, aromatic+C═CHH).

Provenance & Evidence