Borane → (R)-N-(4-methoxy-3-(morpholinosulfonyl)benzyl)-1-(3-chlorophenyl)ethanamine

Participants

Reaction Steps

To a solution of (R)—N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide 43 (0.948 g, 2.16 mmol) in THF (9 mL) at room temperature was added borane (0.124 g, 8.96 mmol) (9 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 50% to 100% EtOAc in hexanes) gave (R)—N-(4-methoxy-3-(morpholinosulfonyl)benzyl)-1-(3-chlorophenyl)ethanamine 44 (0.166 g, 18.1% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.35 (d, J=6.5 Hz, 3H), 3.21-3.24 (m, 4H), 3.55-3.63 (m, 2H), 3.71-3.78 (m, 4H), 3.91 (s, 3H), 6.97 (d, J=8.6 Hz, 1H), 7.20-7.29 (m, 3H), 7.33 (s, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.78 (s, 1H). Mass spectrum: calculated for C20H25ClN2O4S 424.1. found 425.2 (M++1).

Provenance & Evidence