反应详情

温度

0 °C

To a stirred solution of 1,3-dihydro-1-{1-[4-oxocyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one (100 mg) in methanol (4 mL) at 0° C., under nitrogen, was added tert-butylamine-borane (28 mg). The reaction mixture was stirred at 0° C. for 1 h, then quenched with water (2 mL) and concentrated to remove the methanol. The resulting oil was dissolved in ethyl acetate (50 mL) and the organic solution was washed with saturated sodium carbonate (10 mL), then water (10 mL), then brine (10 mL) and then dried over sodium sulfate. Concentration under reduced pressure yielded trans-1,3-dihydro-1-{1-[4-hydroxycyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one (75 mg) as a colorless solid: 1H NMR (400 MHz, CD3 OD) 7.42 (m, 1H), 7.04 (m, 3H), 4.28 (m, 1H), 3.50 (m, 1H), 3.09 (m, 2H), 2.45 (m, 5H), 2.03-1.94 (m, 4H), 1.78-1.75 (m, 2H), 1.44-1.26 (m, 4H). The hydrochloride salt was precipitated from diethyl ether/chloroform: analysis calculated for C18H25N3O2.HCl.0.50 H2O.0.70 CHCl3C: 50.54, H: 6.28, N: 9.45; found C: 50.54, H: 6.19, N: 9.64.

1. customquenched with water (2 mL)
2. concentrationconcentrated
3. customto remove the methanol
4. dissolutionThe resulting oil was dissolved in ethyl acetate (50 mL)
5. washthe organic solution was washed with saturated sodium carbonate (10 mL)
6. dry with materialwater (10 mL), then brine (10 mL) and then dried over sodium sulfate
7. concentrationConcentration under reduced pressure