反应详情

温度

25 °C

A mixture of 2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (80 mg, 0.18 mmol) in tetrahydrofuran (12 mL) and aqueous hydrochloric acid solution (2 N, 6 mL) was stirred at 25° C. for 5 h. The mixture was diluted with ethyl acetate (50 mL), washed with a saturated aqueous sodium bicarbonate solution (2×20 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% dichloromethane/ethyl acetate) afforded 3-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanone (diastereomer 2, 13 mg, 18%) as a white solid: LC/MS m/e calcd for C21H22N2O3S [M+H]+ 383.49, observed 383.0; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (d, J=4.5 Hz, 1H), 7.87-7.94 (m, 3H), 7.60-7.66 (m, 2H), 7.03-7.10 (m, 1H), 6.44 (d, J=3.0 Hz, 1H), 4.35-4.41 (m, 1H), 3.06-3.11 (m, 3H), 2.38-2.49 (m, 1H), 2.07-2.31 (m, 5H), 1.87-1.99 (m, 1H), 1.59-1.71 (m, 1H).

1. washwashed with a saturated aqueous sodium bicarbonate solution (2×20 mL), brine
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated in vacuo
4. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% dichloromethane/ethyl acetate)