反应详情

A solution of (3S)-3-piperidinol hydrochloride (3.00 g, 21.7 mmol, Astatech Inc.), 4-fluoro-2-(methyloxy)-1-nitrobenzene (3.38 g, 19.76 mmol) and potassium carbonate (9.00 g, 65.22 mmol) in dimethylsulfoxide (75 mL) was stirred overnight. The next morning, the reaction was diluted with diethyl ether and saturated aqueous sodium chloride. The ether layer was washed with water, and the combined aqueous layers were subsequently washed twice with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (5% MeOH/CH2CL2) to give (3S)-1-[3-(methyloxy)-4-nitrophenyl]-3-piperidinol as a pale yellow solid (3.90 g, 15.47 mmol, 78% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.71 (m, 2 H), 1.79 (s, 1 H), 1.86-1.96 (m, J=12.96, 6.41, 6.27, 3.48 Hz, 1 H), 1.96-2.04 (m, 1 H), 3.13-3.24 (m, 2 H), 3.47 (ddd, J=12.59, 6.36, 3.20 Hz, 1 H), 3.66 (dd, J=12.82, 3.48 Hz, 1 H), 3.86-3.92 (m, J=7.44, 3.94, 3.74, 3.74 Hz, 1 H), 3.93 (s, 3 H), 6.34 (d, J=2.56 Hz, 1 H), 6.43 (dd, J=9.34, 2.38 Hz, 1 H), 7.98 (d, J=9.34 Hz, 1 H).

1. washThe ether layer was washed with water
2. washthe combined aqueous layers were subsequently washed twice with diethyl ether
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. custompurified by chromatography on SiO2 (5% MeOH/CH2CL2)