Ethyl Acetate → (S)-1-tert-Butyl 2-methyl 2-methyl-5-oxopyrrolidine-1,2-dicarboxylate
Reaction equation
[CH3:1][C@@:2]1([C:14]([O:16][CH3:17])=[O:15])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(OCC)(=[O:20])C>O>[CH3:1][C@@:2]1([C:14]([O:16][CH3:17])=[O:15])[CH2:6][CH2:5][C:4](=[O:20])[N:3]1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]Participants
4
Procedure
To a vigorously stirred solution of (S)-1-tert-butyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate 106B (1 g, 4.11 mmol) in ethyl acetate (40 ml) was added a solution of NaIO4 (3.52 g, 16.46 mmol) and RuCl3 (10 mg, 0.04 mmol) in water (40 ml). The reaction mixture was stirred at room temperature overnight and quenched with isopropanol. The reaction mixture was stirred at room temperature for 20 min and concentrated. The residue was dissolved in ethyl acetate, washed with water and brine, and dried over Na2SO4. The crude product was purified by flash chromatography (20-50% EtOAc/hexane) to give (S)-1-tert-butyl 2-methyl 2-methyl-5-oxopyrrolidine-1,2-dicarboxylate 106C (1.02 g, 100%) as an oil. 1H NMR (CDCl3, 400 MHz) δ 3.74 (s, 3H), 2.51-2.64 (m, 2H), 2.16-2.21 (m, 1H), 1.97-2.02 (m, 3H), 1.65 (s, 3H), 1.46 (s, 9H).