Triethylamine → (S)-5-Biphenyl-4-ylmethyl-1-triethylsilanyl-pyrrolidin-2-one

Participants

Reaction Steps

A dry flask is charged with 1.256 g (5 mmol) (S)-5-biphenyl-4-ylmethylpyrrolidin-2-one (1-a, R1=H) and 15 ml dry THF. To the resulting clear solution, 2.02 g (20 mmol) triethylamine is added followed by 904 mg (6 mmol) triethylchlorosilane (TES-Cl). The reaction mixture is stirred at room temperature for 4 h and then quenched on addition of 5 ml saturated NaHCO3 solution, 10 ml water and 10 ml isopropyl acetate. The layers are separated and the aqueous layer extracted with 10 ml isopropyl acetate. The combined organic layers are dried over MgSO4, filtered and evaporated. The resulting residue is purified by column chromatography (dichloromethane+1% v/v triethylamine) to give (S)-5-Biphenyl-4-ylmethyl-1-triethylsilanyl-pyrrolidin-2-one (1-a, R1=TES) as a yellow oil. NMR (300 MHz, DMSO-d6, δ/ppm): 7.63 (m, 4 H); 7.55 (m, 2 H); 7.32 (m, 3H); 3.80 (m, 1 H); 2.85 (m, 1 H), 2.70 (m, 1 H), 2.10-1.70 (m, 4 H), 1.02-0.80 (m, 15 H). MS (ESI, m/e) 366 [M+H]+; 731 [2M+H]+. IR (solution in CH2Cl2, ν/cm−1): 3426; 3047; 2957; 1698; 1672; 1487; 1378; 1242; 1114; 1008.

Provenance & Evidence