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
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).
Workup
- customquenched with isopropanol
- stirringThe reaction mixture was stirred at room temperature for 20 min
- concentrationconcentrated
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with water and brine
- dry with materialdried over Na2SO4
- customThe crude product was purified by flash chromatography (20-50% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-5f2689384d32460099e23db783a37279
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415340B2
Reaction notes
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