Triethylamine → 4-(5-Bromo-2,3-dihydrobenzofuran-2-yl)-1-(propylsulfonyl)piperidine

Participants

Reaction Steps

To a solution of 4-(5-bromo-2,3-dihydrobenzofuran-2-yl)piperidine (Compound 9A, 185 mg, 0.656 mmol) and Et3N (0.18 mL, 1.311 mmol) in CH2Cl2 (6 mL) at 0° C. was added propane-1-sulfonyl chloride (140 mg, 0.983 mmol). Upon completion of addition, the reaction mixture was warmed to room temperature, where it stirred for 2 hours. After this time, the reaction mixture was diluted with CH2Cl2 (5 mL) and washed with aqueous NaHCO3 (saturated, 5 mL). The organic layer was separated, dried (Na2SO4), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, hexanes/EtOAc gradient 0 to 50% EtOAc) to afford Compound 10A as a white solid (213 mg, 0.549 mmol, 84% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.27-7.25 (m, 1 H), 7.21 (dd, J=8.4, 2.1 Hz, 1 H), 6.63 (d, J=8.3 Hz, 1 H), 4.63-4.53 (m, 1 H), 3.93-3.84 (m, 2 H), 3.22 (dd, J=15.7, 9.1 Hz, 1 H), 2.96 (dd, J=15.8, 8.1 Hz, 1 H), 2.91-2.86 (m, 2 H), 2.80-2.71 (m, 2 H), 2.05-1.99 (m, 1 H), 1.90-1.81 (m, 2 H), 1.80-1.71 (m, 2 H), 1.53-1.41 (m, 2 H), 1.07 (t, J=7.4 Hz, 3 H). LC/MS (m/z)=389 (M+H)+.

Provenance & Evidence