Water → Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

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Reaction Steps

4-Fluoro-nitrobenzene (0.728 mL, 6.96 mmol) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (A110) (1.40 g, 6.96 mmol) and potassium tert-butoxide (1.09 g, 9.74 mmol) in anhydrous DMSO (7.5 mL) and the resulting mixture was stirred for 2 hours at room temperature. Water and EtOAc were added to the mixture and the phases were separated. The aqueous phase was extracted with EtOAc, then the combined organic extracts were washed with water, brine and dried over Na2SO4. The volatiles were evaporated under reduced pressure and the residue was adsorbed onto silica gel and purified by column chromatography (SiO2 cartridge, 0-15% EtOAc in cyclohexane) to give the title compound A111 as an oil (2.20 g, 98%); 1H NMR (300 MHz, CDCl3); δ 8.09 (d, J=9.4 Hz, 2H), 6.91 (d, J=9.3 Hz, 2H), 4.58 (m, 1H), 3.65 (m, 2H), 3.33 (m, 2H), 1.92 (m, 2H), 1.72 (m, 2H), 1.41 (s, 9H). LCMS-B: rt 8.22 min; m/z 323.3 [M+H]+.

Provenance & Evidence