Isopropyl Acetate → 5-(4-tert-Butylphenyl)-4-(phenylsulfonyl)pyrrolidine-2-carboxylic Acid Ethyl Ester

Participants

Reaction Steps

To a stirred solution of (E)-ethyl 2-(4-tert-butylbenzylideneamino)acetate (226 mg, 914 umol; example 441a) in THF (5 ml) under an argon atmosphere were added lithium bromide (119 mg, 1.37 mmol), triethylamine (191 ul, 1.37 mmol) and phenyl vinyl sulfone (154 mg, 914 umol; CAS Reg. No. 5535-48-8). The mixture was stirred at ambient temperature for 20 h. iPrOAc (50 ml) and ice water (40 ml) were added and the layers were separated. The organic layer was washed with brine (40 ml), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, iPrOAc/n-heptane) to obtain the title compound (56 mg, 73 umol; 8%) as colorless solid. MS (ESI): m/z=416.2 [M+H]

Provenance & Evidence