OC(C)(C)[C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].CC(C)([O-])C.[K+].CCOC(C)=O>C1COCC1.CCCCCC>[CH3:17][C:14]1([CH3:16])[O:13][C:12](=[O:18])[NH:11][C@H:3]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10]To a solution of (S)-tert-butyl (2-hydroxy-2-methyl-1-(o-tolyl)propyl)carbamate (1 g, 3.5 mmol) in THF (20 mL) was added potassium tert-butoxide (803.37 mg, 7.1 mmol) at 0-5° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layers were washed with, water, washed with saturated NaCl solution, dried with Na2SO4, filtered and evaporated to afford (S)-5,5-dimethyl-4-(o-tolyl)oxazolidin-2-one, 0.7 g (95.28% Y) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.96 (s, 1H), 7.27-7.25 (m, 1H), 7.22-7.19 (m, 3H), 4.83 (s, 1H), 2.29 (s, 3H), 1.55 (s, 3H), 0.81 (s, 3H). m/z (ESI) 206.1 (M+H)+.
Loading…
