Trimethylsilyl iodide → HCID 57988323, compound

Participants

Reaction Steps

To a solution of (2S,4R)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-(propylsulfonyl)pyrrolidine-1,2-dicarboxylate (1.85 g, 3.55 mmol) in acetonitrile (30 mL) was added iodotrimethylsilane (1.211 mL, 8.51 mmol) at 0° C. The formed light brown solution was stirred at room temperature for 2 h. Cooled with ice bath, quenched with methanol. Removed the volatiles in vacuo. The residual brown oil was triturated with 2M HCl in ether (20 mL). The formed brown solid was filtered. Washed the cake with ether thoroughly. The collected light brown solid was pumped to afford the desired product (2S,4R)-methyl 4-(biphenyl-4-yl)-4-(propylsulfonyl)pyrrolidine-2-carboxylate (1.54 g, 3.19 mmol, 90% yield). 1H NMR (500 MHz, MeOD) δ ppm 0.97 (t, J=7.32 Hz, 3 H) 1.57-1.71 (m, 2 H) 2.96 (dd, J=9.16, 5.49 Hz, 1 H) 3.22-3.39 (m, 2 H) 3.65 (dd, J=15.72, 4.73 Hz, 1 H) 3.94 (s, 1 H) 4.14 (d, J=13.12 Hz, 1 H) 4.70 (d, J=13.12 Hz, 1 H) 7.37-7.44 (m, 1 H) 7.45-7.54 (m, 2 H) 7.66 (dd, J=19.99, 7.78 Hz, 4 H) 7.79 (d, J=8.55 Hz, 2 H). LC-MS (retention time: 1.42 min, method A), MS m/z 388 (M+H).

Provenance & Evidence