Benzyl Bromide → (S)-2-(Dibenzylamino)butan-1-ol

Participants

Reaction Steps

To a stirred solution of (S)-(+)-2-aminobutan-1-ol (5 g, 56.18 mmol) in dry acetonitrile (100 ml) was added dry powdered potassium carbonate (31 g, 224.72 mmol) followed by benzyl bromide (19 g, 111.11 mmol). The reaction was stirred at room temperature for 24 h. The solvent was removed under vacuo and the residue was taken up in ethyl acetate (100 ml) and water (100 ml). The organic phase was washed again with water, dried (Na2SO4) and concentrated to provide the pure product as slightly yellow oil (14.5 g, 97.3%). δH (250 MHz, CDCl3) 0.98 (3 H, t, J 7.5, CHCH2CH3), 1.38-1.2 (1 H, m, CHCHHCH3), 1.94-1.78 (1 H, m, CHHCH3), 2.83-2.71 (1 H, m, CHCHHCH3), 3.22 (1 H, s, b, OH), 3.65-3.4 (2 H, m, CH2OH), 3.47 (2 H, d, J 17.5, 2×CHHPh), 3.94 (2 H, d, J 17.5, 2×CHHPh), 7.46-7.26 (10 H, m, 2×C6H5); δC (250 MHz, CDCl3) 139.42 (2×C), 129.1 (2×CH), 128.52 (2×CH), 127.25 (2×CH), 61.97 (CH), 60.67 (CH2), 53.23 (CH2), 17.92 (CH2), 11.83 (CH3); m/z 270.2 (M+H)

Provenance & Evidence