Imidazole → (S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

Participants

Reaction Steps

A stirred solution of commercial (S)-3-hydroxypyrrolidin-2-one (5 g, 50 mmol) in DCM (198 ml) was treated with DMAP (0.2 g, 1.63 mmol), imidazole (6.73 g, 99 mmol), and TBDMS-Cl (8.94 g, 59 mmol). The reaction mixture was stirred at rt for 16 h, and then was washed with a satd. NaHCO3 solution. The organic layer was concentrated and the crude reaction product was purified by silica gel chromatography, eluting with 50% ethyl acetate in petroleum ether. The desired product was isolated as a white solid (8.1 g, 76%). LC/MS (M+H)+=216.2; 1H NMR (400 MHz, chloroform-d) δ 6.40 (br. s., 1H), 4.26 (t, J=7.8 Hz, 1H), 3.42-3.34 (m, 1H), 3.29-3.21 (m, 1H), 2.36 (dtd, J=12.7, 7.3, 3.3 Hz, 1H), 2.07-1.96 (m, 1H), 0.91 (s, 9H), 0.15 (d, J=7.0 Hz, 6H).

Provenance & Evidence