Toluene → HCID 86673650, compound

Participants

Reaction Steps

Sodium hydride (2.03 g, 46.4 mmol) is suspended in 40-mL of anhydrous toluene, heat to reflux under nitrogen atmosphere, add a mixture solution of (S)-5-Biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-pyrrolidin-2-one (3a, R1=1-butenyl) (11.02 g, 35.67 mmol) and methyl benzoate (4.86 g, 35.67 mmol) in anhydrous toluene dropwise, the reaction mixture is refluxed for 4 h, cool to ambient temperature, quench with saturated NH4Cl aqueous solution, extracted with toluene, the combined organic extracts are washed with saturated Na2CO3 and brine, dry over anhydrous Na2SO4, concentrate under vacuum to obtain (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-pyrrolidin-2-one (4a, R1=1-butenyl, R4=benzyl), which is directly used in the next step. 1HNMR (400 MHz, CDCl3): 1.07 (t, 3H, CH3H), 2.12 (m, 2H, CH2H), 2.20 (m, 2H, 3-CH2), 2.95 (m, 1H, 5-CH2), 3.13 (m, 1H, 5-CH2), 3.82 (m, H, 2-CH2H), 4.14 (m, 1H, 4-CH), 5.27 (m, 1H, CH═CH), 6.85 (d, 1H, HC═CH—N), 7.14˜8.20 (14H, m, aromatic). the ratio of (3S,5S) to (3R,5S) is 60:40 as determined by HPLC.

Provenance & Evidence