反应详情

温度

85 °C

To a solution of spiro-[indene-1,4-piperidine]trifluoroacetate (4 g, 14 mmol) in ethanol (25 mL) is added ethyl 4-(bromomethyl)-benzoate (2.9 g, 12.6 mmol), followed by diisopropylethylamine (9.6 mL, 56 mmol). The reaction mixture is refluxed at 85° C. for overnight. The ethanol is removed under reduced pressure and the residue is partitioned between EtOAc (150 mL) and water (50 mL). The organic layer is washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography, eluting with hexane:ethyl acetate (8.0:2.0) to give the title compound as brown solid (2.8 g, 60%). 1H NMR (400 MHz) 7.94 (d, J=8 Hz, 2H), 7.51 (d, J=8 Hz, 2H), 7.43 (d, J=7.2 Hz, 1H), 7.31 (d, J=7.2 Hz, 1H), 7.18 (m, J=7.2 Hz, 2H), 6.94 (d, J=5.6 Hz, 1H), 6.78 (d, J=5.6 Hz, 1H), 4.30 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), 2.85 (d, J=11.6 Hz, 2H), 2.38 (t, J=11.6 Hz, 2H), 2.09 (t, J=10.4 Hz, 2H), 1.31 (t, J=7.2 Hz, 2H), 1.19 (d, J=12.8 Hz, 2H).

1. customThe ethanol is removed under reduced pressure
2. customthe residue is partitioned between EtOAc (150 mL) and water (50 mL)
3. washThe organic layer is washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue is purified by silica gel chromatography
8. washeluting with hexane:ethyl acetate (8.0:2.0)