Dichloromethane → HCID 58641265, compound

Participants

Reaction Steps

A solution of tert-butyl (2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (5-5, 100 mg, 0.280 mmol, 1 equiv) in a 4:1 mixture of dichloromethane and trifluoroacetic acid (20 mL) was stirred for 30 min, then concentrated. The residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and were concentrated. A solution of the residue and methyl vinyl sulfone (0.025 mL, 0.28 mmol, 1.0 equiv) in a 1:1 mixture of dioxane and ethanol (5 mL) was stirred at 23° C. for 16 h. Additional methyl vinyl sulfone (0.025 mL, 0.28 mmol, 1.0 equiv) was added and stirring was continued for 4 h. The reaction mixture was concentrated and the residue was purified by flash column chromatography (hexanes initially, grading to 50% EtOAc in hexanes) to give (2S)-4-(2,5-difluorophenyl)-1-[2-(methylsulfonyl)ethyl]-2-phenyl-2,5-dihydro-1H-pyrrole (37-1) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.38-7.28 (m, 5H), 7.09-6.89 (m, 3H), 6.28 (br s, 1H), 4.69 (td, 1H, J=4.9, 1.8 Hz), 4.34 (dd, 1H, J=12.5, 4.9 Hz), 3.84 (ddd, 1H, J=13.0, 4.8, 1.7 Hz), 3.36-3.02 (m, 4H), 2.79 (s, 3H). LRMS m/z (M+H) 364.3 found, 364.1 required.

Provenance & Evidence