反应详情

温度

100 °C

To a solution of 4-benzyl-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (0.65 mmol) in 1,4-dioxane (2 mL) are added Et3N (0.71 mmol) and DPPA (0.71 mmol) at room temperature. After warming to 100° C. and stirring for 2 h, the reaction mixture is diluted with AcOEt. The organic layer is washed with sat. aq. NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue is dissolved in THF (4 mL) and 6N aq. NaOH (0.22 mL) is added at room temperature. After stirring for 4 h, the reaction mixture is diluted with CH2Cl2, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography to give the title compound; 1H NMR (CDCl3), δ: 1.18 (2H, bs), 1.28-1.37 (2H, m), 1.46 (9H, s), 1.51-1.64 (2H, m), 2.66 (2H, s), 3.20 (2H, dd), 3.74 (2H, bd), 7.13-7.19 (2H, m), 7.21-7.34 (3H, m).

1. washThe organic layer is washed with sat. aq. NaHCO3 and brine
2. dry with materialdried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. dissolutionThe residue is dissolved in THF (4 mL)
6. addition6N aq. NaOH (0.22 mL) is added at room temperature
7. stirringAfter stirring for 4 h
8. additionthe reaction mixture is diluted with CH2Cl2
9. washwashed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe residue is purified by silica gel column chromatography