Imidazole → (S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

참여 물질

반응 단계

Imidazole (4.09 g, 60 mmols) and 4-dimethylaminopyridine (100 mg, 0.82 mmol) were added to a CH2Cl2 (85 ml) solution of (5S)-5-(hydroxymethyl)-2-pyrrolidinone (3.14 g, 27.3 mmols). Then, with the mixture being cooled with ice, a CH2Cl2 (15 ml) solution of tert-butyldimethylsilyl chloride (4.53 g, 30 mmols) was added, and the mixture was stirred for 15 hours at room temperature. The solvent was distilled off under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 300 g, MeOH—CHCl3 5:95 v/v) to obtain (5S)-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidin-2-one (6.22 g, 99.5%): [α]D27+42.32 (c 1.136, CHCl3). IR νmax (film) cm−1: 3242, 1697. 1H-NMR (CDCl3)δ: 5.79 (1H, br), 3.80-3.71 (1H, m), 3.63 (1H, dd, J=9.9, 3.8 Hz), 3.44 (1H, dd, J=9.9, 7.7 Hz), 2.44-2.26 (2H, m), 2.24-2.11 (1H, m), 1.80-1.67 (1H, m), 0.89 (9H, s), 0.06 (6H, s). MS m/z: 230 (M++1), 214 (M+−15), 172 (100%). HRMS: Calculated for C10H20NO2Si: 214.1263 (M+−15). Found: 214.1240 (M+−15).

출처 및 근거