反应详情

tert-Butyl 4-((3-bromo-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (1.36 g, 2.69 mmol) and tin (II) chloride dihydrate (6.48 g, 28.7 mmol) were combined in ethyl acetate (20 mL) and heated at reflux for 4 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate and concentrated. The crude product was dissolved in tetrahydrofuran (10 mL), cooled to 0° C. and treated with di-tert-butyl carbonate (0.59 g, 2.69 mmol) and 10 N sodium hydroxide (0.65 mL). The reaction was allowed to warm to room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water (2×), brine (2×), dried over sodium sulfate and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) gave 0.25 g (19%). LC/MS (HPLC method 3): tR=2.99 min, 477.05 (MH)+.

1. temperatureheated
2. temperatureat reflux for 4 h
3. washwashed with saturated sodium bicarbonate (2×), brine (2×)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. dissolutionThe crude product was dissolved in tetrahydrofuran (10 mL)
7. temperaturecooled to 0° C.
8. temperatureto warm to room temperature overnight
9. washwashed with water (2×), brine (2×)
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated
12. customColumn chromatography on silica gel (30% ethyl acetate/hexanes) gave 0.25 g (19%)