反应详情

To a solution of benzyl (3R,4R)-3,4-dihydroxypyrrolidine-1-carboxylate (3.81 g, 16.1 mmol) in 60 mL THF was added NaH (0.803 g, 20.07 mmol). The reaction mixture was stirred at room temperature for 15 min, CH3I (2.0 mL, 32.2 mmol) was added and stirred at room temperature overnight. The reaction mixture was quenched with H2O (80 mL) and extracted with EtOAc (2×100 mL). The organic layer was dried and concentrated. The residue was purified by flash column chromatography (1˜2% CH3OH in CH2Cl2) to give a white solid (1.12 g, 28%). 1H NMR (CDCl3) δ 7.36-7.29 (5H, m), 5.12 (2H, s), 4.28-4.27 (1H, m), 3.72-3.37 (5H, m), 3.35 (3H, s), 1.95-1.89 (1H, m). ESIMS (MH+): 252.05.

1. stirringstirred at room temperature overnight
2. customThe reaction mixture was quenched with H2O (80 mL)
3. extractionextracted with EtOAc (2×100 mL)
4. customThe organic layer was dried
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatography (1˜2% CH3OH in CH2Cl2)