Triethylamine → N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(trifluoromethyl)pyridine-3-sulfonyl chloride (190 mg, 0.78 mmol) in 2 mL dichloromethane was added dropwise to a solution of ((1R,2R)-2-aminocyclohexyl)methanol (100 mg, 0.78 mmol) and triethylamine (320 μL, 2.3 mmol) in 10 mL dichloromethane at 0° C. The reaction was stirred at 0° C. for 1 h, then concentrated and purified by flash chromatography on silica gel with 0 to 60% ethyl acetate in hexane to yield N-((1R,2R)-2-(hydroxymethyl)cyclohexyl)-6-(trifluoromethyl)pyridine-3-sulfonamide (150 mg, 57%). 1H NMR (400 MHz, CDCl3) δ ppm 9.18 (d, J=2.01 Hz, 1H), 8.37 (dd, J=8.06, 1.76 Hz, 1H), 7.83 (d, J=8.31 Hz, 1H), 5.83 (d, J=6.80 Hz, 1H), 3.77 (ddd, J=11.21, 3.78, 3.65 Hz, 1H), 3.36 (dt, J=11.33, 5.67 Hz, 1H), 2.97-3.15 (m, 1H), 2.37 (t, J=5.41 Hz, 1H), 1.73-1.87 (m, 1H), 1.67 (d, J=2.01 Hz, 1H), 1.56-1.66 (m, 2H), 1.33-1.46 (m, 1H), 1.05-1.30 (m, 4H). MS [M+H]+=339. MS [M+Na]+=361.

Provenance & Evidence