4-Chlorobenzenesulfonyl chloride → 2-(4-Chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol

Participants

Reaction Steps

To a solution of 2-aminobicyclo[2.2.1]heptan-7-ol (prepared according to U.S. Pat. No. 5,583,221) (1.29 g, 10.1 mmol) and triethylamine (1.67 mL, 12 mmol) in 75 mL tetrahydrofuran was added 4-chlorobenzenesulfonyl chloride (2.53 g, 12 mmol). The reaction was stirred at room temperature for 2 h, then diluted into 150 mL ethyl acetate and washed with brine (100 mL). The organic layer was concentrated and purified by flash chromatography on a 40 g silica gel column using a gradient of 10 to 50% ethyl acetate in hexane over 25 min to give 2-(4-chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol (2.12 g, 70%). 1H NMR (400 MHz, CDCl3) δ ppm 7.79-7.81 (1H, m), 7.77-7.79 (1H, m), 7.46-7.48 (1H, m), 7.44-7.46 (1H, m), 5.61 (1H, d, J=10.32 Hz), 4.00 (1H, s), 3.34-3.48 (1H, m), 2.00-2.04 (1H, m), 1.86 (1H, d, J=3.78 Hz), 1.83 (1H, br. s.), 1.68-1.76 (1H, m), 1.59-1.66 (1H, m), 1.37-1.54 (2H, m), 0.97-1.09 (2H, m). LC/MS R.T.=1.98 min; [M+H]+=302.16.

Provenance & Evidence