Isopropyl chloroformate → HCID 59177770, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-2-[4-(methylsulfonyl)phenyl]-5-{[1-(4-piperidinyl)ethyl]oxy}pyridine (0.27 g, 0.75 mmol) in CH2Cl2 (10 mL) and THF (5 mL) was treated with diisopropylethylamine (0.27 mL, 1.50 mmol). The mixture was cooled to 0° C., and then isopropyl chloroformate (1.0M in toluene, 0.82 mL, 0.82 mmol) was added dropwise. The reaction mixture was allowed to warm to ambient temperature and stirred overnight, diluted with CH2Cl2 (100 mL) and washed with water, brine and dried over Na2SO4, filtered, and the filtrate was concentrated to a light brown oil. The crude material was purified by flash chromatography on a silica gel column eluted with 1:5 acetone/CH2Cl2 to give 0.31 g (93%) of the title compound as a white foam. 1H NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=2.9 Hz), 8.13 (d, 2H, J=8.5 Hz), 8.01 (d, 2H, J=8.5 Hz), 7.73 (d, 1H, J=8.8 Hz), 7.35-7.25 (m, 1H), 4.91 (septet, 1H, J=6.2 Hz), 4.35-4.15 (m, 3H), 3.08 (s, 3H), 2.80-2.65 (m, 2H), 1.95-1.65 (m, 3H), 1.45-1.25 (m, 5H), 1.23 (d, 6H, J=6.3 Hz); LRMS (ESI), m/z 447 (M+H).

Provenance & Evidence