Methanol → (2S,4R)-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-2-carboxylate

Participants

Reaction Steps

To an iced solution of (2S,4R)-1-benzyl 2-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-1,2-dicarboxylate (1.85 g, 3.79 mmol) in acetonitrile (20 mL) was added iodotrimethylsilane (0.810 mL, 5.69 mmol). The formed light brown solution was stirred at room temperature for 2 h. Cooled with ice bath, quenched with methyl alcohol (7.68 mL, 190 mmol). The formed light brown solution was purified by prep-HPL, and the collected fractions were evaporated on speed-vac system. The yellow residue was taken up in DCM, washed with sat. Na2CO3 and brine, dried over MgSO4, filtered, evaporated in vacuo to afford the desired product (2S,4R)-methyl 4-(allylthio)-4-(biphenyl-4-yl)pyrrolidine-2-carboxylate (664 mg, 1.878 mmol, 49.5% yield) as a viscous oil. 1H NMR (500 MHz, MeOD) δ ppm 2.93-3.08 (m, 3H) 3.11-3.20 (m, 1H) 3.77-3.88 (m, 1H) 3.92-3.99 (m, 3H) 4.04 (d, J=12.21 Hz, 1H) 4.72-4.80 (m, 1H) 5.02 (d, J=9.77 Hz, 1H) 5.09 (dd, J=16.94, 1.37 Hz, 1H) 5.54-5.70 (m, 1H) 7.35-7.42 (m, 1H) 7.43-7.56 (m, 4H) 7.60-7.68 (m, 2H) 7.69-7.77 (m, 2H). LC-MS (retention time; 2.21 min, method A), MS m/z 354 (M+H).

Provenance & Evidence