Borane → (R)-2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)benzenesulfonamide

Participants

Reaction Steps

To a solution of 3-(aminosulfonyl)-4-chloro-N-((1R)-1-(3-chlorophenyl)ethyl)benzamide 38 (0.558 g, 1.49 mmol) in THF (10 mL) at room temperature was added borane (0.138 g, 9.97 mmol) (10 mL, 1 M in THF). The reaction mixture was heated to reflux for 24 h, quenched with 1 M NaOH, and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 40% to 80% EtOAc in hexanes) gave (R)-2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)benzenesulfonamide 39 (0.210 g, 39.1% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.36 (d, J=6.5 Hz, 3H), 3.64 (s, 2H), 3.76 (q, J=6.6 Hz, 1H), 5.20 (s br, 2H), 7.19-7.31 (m, 5H), 7.44-7.46 (m, 2H), 8.01 (s, 1H). Mass spectrum: calculated for C15H16Cl2N2O2S 358.0. found 359.1 (M++1).

Provenance & Evidence