反应详情

温度

0 °C

Phenylmethyl 4-[(3-methyl-4-nitrophenyl)oxy]-1-piperidinecarboxylate (0.798 g, 2.15 mmol) was dissolved in 20 mL of MeOH with stirring. Nickel(II) chloride hexahydrate (0.256 g, 1.08 mmol) was added and the mixture was cooled to 0° C. Sodium borohydride (0.163 g, 4.31 mmol) was added, and the mixture was stirred for 20 min. Additional sodium borohydride (˜20 to 30 mg) was added, and the mixture was stirred for 10 min more. The reaction was quenched by the addition of approximately 15 mL of 2N sodium hydroxide solution. The mixture was poured into EtOAc and H2O, and the layers were separated. The organic layer was washed with brine, and the combined aqueous layers were extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford 0.568 g (78%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.40-7.23 (m, 5H), 6.61-6.43 (m, 3H), 5.04 (s, 2H), 4.37 (s, 2H), 4.27-4.17 (m, 1H), 3.74-3.57 (m, 2H), 3.27-3.12 (m, 2H), 1.97 (s, 3H), 1.86-1.73 (m, 2H), 1.52-1.39 (m, 2H).

1. stirringthe mixture was stirred for 20 min
2. stirringthe mixture was stirred for 10 min more
3. customThe reaction was quenched by the addition of approximately 15 mL of 2N sodium hydroxide solution
4. additionThe mixture was poured into EtOAc and H2O
5. customthe layers were separated
6. washThe organic layer was washed with brine
7. extractionthe combined aqueous layers were extracted with EtOAc
8. dry with materialThe combined organic layers were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography