Potassium tert-butoxide → HCID 89814013, compound

Reaction equation

CC(C)([O-])C.[K+].OC(C)(C)[CH:9]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])C)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1>C1COCC1.C(Cl)Cl>[CH3:22][C:19]1([CH3:21])[O:18][C:17](=[O:23])[NH:16][CH:9]1[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

Procedure

Potassium tert-butoxide (0.093 g, 0.826 mmol) was added to a 0° C. solution of tert-butyl (2-hydroxy-2-methyl-1-(pyridin-3-yl)propyl)carbamate (0.200 g, 0.751 mmol) in THF (5.0 mL). The ice bath was removed and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated to afford a yellow oil. The residual yellow oil was dissolved in DCM and passed through a Silycycle SCX column washing with MeOH and then with 7 N ammonia in MeOH. The ammonia solution was concentrated to afford 5,5-dimethyl-4-(pyridin-3-yl)oxazolidin-2-one (0.150 g, 0.780 mmol, 100% yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82 (s, 3H), 1.53 (s, 3H), 4.74 (s, 1H), 7.44 (ddd, J=7.90, 4.77, 0.64 Hz, 1H), 7.64-7.78 (m, 1H), 8.08 (s, 1H), 8.51 (d, J=2.35 Hz, 1H), 8.55 (dd, J=4.79, 1.66 Hz, 1H). m/z (ESI) 193 (M+H)+.