Borane → (R)-N-(4-chloro-3-(phenylthio)benzyl)-1-(3-chlorophenyl)ethanamine

Participants

Reaction Steps

To a solution of (R)-4-chloro-N-(1-(3-chlorophenyl)ethyl)-3-(phenylthio)benzamide 33 (0.631 g, 1.57 mmol) in THF (8 mL) was added borane (0.110 g, 7.95 mmol) (8 mL, 1 M in THF). The reaction mixture was heated to reflux for 2 d, 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 20% to 50% EtOAc in hexanes) gave (R)—N-(4-chloro-3-(phenylthio)benzyl)-1-(3-chlorophenyl)ethanamine 34 (0.274 g, 45.0% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.26 (d, J=6.5 Hz, 3H), 3.41 (d, J=13.7 Hz, 1H), 3.50 (d, J=13.7 Hz, 1H), 3.65 (q, J=6.7 Hz, 3H), 6.93 (s, 1H), 7.05-7.09 (m, 2H), 7.20-7.25 (m, 2H), 7.37-7.43 (m, 6H). Mass spectrum: calculated for C15H14Cl2NS 387.1. found 388.1 (M++1).

Provenance & Evidence