反应详情

温度

80 °C

To a stirred solution of 1-tert-butoxycarbonyl-4-piperidone (14.9 g, 74.8 mmol) in DMF (35 mL) was added TMSCl (11.4 mL, 89.7 mmol) and then Et3 N (25.0 mL, 179 mmol) dropwise at room temperature, and the reaction mixture was heated at 80° C. for 18 hr. Hexane was added to the reaction mixture, and the resulting mixture was washed with sat. NaHCO3 and brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with hexane-EtOAc (5:1, v/v) as eluent gave 1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-4-(trimethylsilyloxy)pyridine (20.4 g, 99%) as a yellow oil. 1H-NMR (CDCl3) δ 0.19 (s, 9H), 1.46 (s, 9H), 2.05–2.15 (m, 2H), 3.48–3.56 (m, 2H), 3.83–3.91 (m, 2H), 4.79 (broad s, 1H).

1. washthe resulting mixture was washed with sat. NaHCO3 and brine
2. dry with materialdried over Na2SO4
3. concentrationconcentrated to dryness