反应详情

温度

45 °C

To a solution of ethyl 2-(2-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (143 mg, 0.286 mmol) in dioxane (1.5 mL) was added 1 M LiOH aqueous solution (1.15 mL, 1.145 mmol). The reaction mixture was stirred at 45° C. for 3 h. A portion of the solvent was removed in vacuo. The remaining mixture was diluted with water, acidified with 0.5 M aqueous citric acid to pH 4, and extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated to give the title compound (105 mg). LCMS m/z=472.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.54-1.66 (m, 3H), 1.67-1.80 (m, 2H), 1.80-1.92 (m, 2H), 2.00-2.24 (m, 5H), 2.64 (dd, J=16.1 and 8.7 Hz, 1H), 3.01 (dd, J=16.1 and 5.3 Hz, 1H), 3.33-3.42 (m, 1H), 3.45-3.55 (m, 1H), 3.85-3.94 (m, 1H), 4.12-4.18 (m, 1H), 5.08 (s, 2H), 6.22 (s, 1H), 6.90 (dd, J=8.8 and 2.4 Hz, 1H), 7.10 (d, J=2.4 Hz, 1H), 7.17 (d, J=8.8 Hz, 1H), 7.47 (d, J=8.1 Hz, 1H), 7.59 (d, J=8.1 Hz, 1H), 7.70 (s, 1H).

1. customA portion of the solvent was removed in vacuo
2. additionThe remaining mixture was diluted with water
3. extractionextracted with ethyl acetate
4. washThe combined organics were washed with water
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated