Methyl Benzoate → HCID 86673650, compound

Participants

Reaction Steps

(S)-5-Biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (3a, R1=styryl) (1.00 g, 2.8 mmol) is heated to dissolve in 3 mL of anhydrous toluene under N2, add t-BuOK (0.43 g, 3.7 mmol) in one portion, stir at this temperature for 10 min, then add methyl benzoate dropwise, the reaction mixture reflux overnight, cool to room temperature, quench with saturated NH4Cl aqueous solution, separate the organic phase, extract with toluene (30 mL*3), the combined organic extracts are washed with saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4 and concentrate under vacuum. The residue is purified by silica gel column chromatography, eluting with 5:1 heptane/ethyl acetate 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. Spectroscopic data as Example 8, Method 1.

Provenance & Evidence