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

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 vaccuo 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 (1H, 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 (2H, 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)

1. customThe solvent was removed under vaccuo
2. washThe organic phase was washed again with water
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated

ORD record

ord-149e77a445eb4131997b9ba25ed7835c

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592581B2