Potassium Carbonate → HCID 59860244, compound

Participants

Reaction Steps

A solution of (3S)-3-piperidinol hydrochloride (3.00 g, 21.7 mmol), 5-fluoro-2-nitrophenyl methyl ether (Example 22, step A) (3.38 g, 19.76 mmol) and K2CO3 (9.00 g, 65.22 mmol) in DMSO (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 thrice with H2O, and the combined aqueous layers were subsequently washed twice with diethyl ether. The combined organic layers were dried over Na2SO4, taken to a residue under reduced pressure, and purified by chromatography on SiO2 to give the title compound 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, 2H), 1.79 (s, 1H), 1.86-1.96 (m, J=12.96, 6.41, 6.27, 3.48 Hz, 1H), 1.96-2.04 (m, 1H), 3.13-3.24 (m, 2H), 3.47 (ddd, J=12.59, 6.36, 3.20 Hz, 1H), 3.66 (dd, J=12.82, 3.48 Hz, 1H), 3.86-3.92 (m, J=7.44, 3.94, 3.74, 3.74 Hz, 1H), 3.93 (s, 3H), 6.34 (d, J=2.56 Hz, 1H), 6.43 (dd, J=9.34, 2.38 Hz, 1H), 7.98 (d, J=9.34 Hz, 1H).

Provenance & Evidence