4-Chlorobenzenesulfonyl chloride → 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide

Participants

Reaction Steps

To a solution of trans-2-aminocyclopentylmethanol (prepared according to LaPlae et al., J. Org. Chem., 66:5629-5632 (2001)) (1.05 g, 7.5 mmol) and triethylamine (1.25 mL, 9.0 mmol) in 25 mL tetrahydrofuran was added 4-chlorobenzenesulfonyl chloride (1.90 g, 9.0 mmol). The reaction was stirred at room temperature for 2 h, then diluted into 100 mL ethyl acetate and extracted with brine (50 mL). The organic layer was concentrated and purified by flash chromatography on a 40 g silica gel column using a gradient of 20 to 80% ethyl acetate in hexane over 30 min to give 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide (1.61 g, 74%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.85 (2H, m), 7.42-7.52 (2H, m), 5.10 (1H, d, J=6.29 Hz), 3.70 (1H, ddd, J=10.64, 5.22, 5.04 Hz), 3.41-3.53 (1H, m), 3.21-3.33 (1H, m), 1.70-1.98 (4H, m), 1.44-1.68 (3H, m), 1.31-1.44 (1H, m). LC/MS R.T.=2.33 min; [M+H]+=290.06.

Provenance & Evidence