反应详情

温度

0 °C

To a solution of 5-(3-oxo-4-phenyl-butyl)-pyrrolidin-2-one (5.902 g, 25.52 mmol) in EtOH (30 mL) at 0° C. was added NaBH4 (485 mg, 12.76 mmol) and the reaction mixture was stirred at 0° C. for 2.5 h. The reaction mixture was quenched with saturated aqueous ammonium chloride. Water and CH2Cl2 were added. The aqueous layer was washed with CH2Cl2 (2×) and the combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2) to yield 4.3 g of 5-(3-hydroxy-4-phenyl-butyl)-pyrrolidin-2-one. 1H NMR (CDCl3) δ7.35–7.16 (m, 5H), 6.02 (m, 1H), 3.80 (m, 1H), 3.63 (m, 1H), 2.79 (m, 1H), 2.64 (m, 1H), 2.26 (m, 3H), 1.72–1.22 (m, 6H).

1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
2. additionWater and CH2Cl2 were added
3. washThe aqueous layer was washed with CH2Cl2 (2×)
4. dry with materialthe combined organic extracts were dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by medium pressure chromatography with a solvent gradient (1:1 hexanes:EtOAc to EtOAc to 1% MeOH in CH2Cl2)