Methyl Benzoate → HCID 86673650, compound

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Reaction Steps

(S)-5-Biphenyl-4-ylmethyl-1-((E)-styryl)-pyrrolidin-2-one (3a, R1=styryl) (10.0 g, 28.3 mmol) is heated to dissolve in 30 mL of anhydrous toluene under N2, add MeONa (1.99 g, 36.8 mmol) in one portion, stir at this temperature for 10 min, then add methyl benzoate dropwise, reflux overnight, cool to room temperature, quench with saturated NH4Cl aqueous solution, separate the organic phase, extract with toluene (15 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 give (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