Formaldehyde → HCID 53312154, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-Benzoyl-5-biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-pyrrolidin-2-one (4a, R1=1-butenyl, R4=phenyl) (5.5 g, 13.2 mmol) in 25 mL of tetrahydrofuran is added 1 M K2CO3 aqueous solution (26.4 mL, 26.4 mmol), 37% CH2O aqueous solution (2.2 mL, 26.4 mmol) and n-Bu4NOH (0.4 mL, 0.7 mmol), heat to 45° C. under N2 for 2 h, cool to room temperature, extract with toluene, the combined organic layer are washed with 5% HCl(aq), saturated Na2CO3 aqueous solution and brine, dry over anhydrous Na2SO4, evaporate the solvent, the residue is purified by column chromatography to obtain (R)-5-Biphenyl-4-ylmethyl-1-((E)-but-1-enyl)-3-methylene-pyrrolidin-2-one (1a, R1=1-butenyl). Spectroscopic data as Example 24, Method 1.

Provenance & Evidence