Diethyl Ether → HCID 18672299, compound

Participants

Reaction Steps

1M LAH in ether (11.25 mL, 11.25 mmol) was added to a stirred solution of 5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzonitrile (1.67 g, 7.50 mmol) in THF (70 mL) at 0° C. After 1 h the reaction was quenched with EtOAc (5 ml) and concentrated. The residue was stirred with ether (150 mL) and this was then treated successively with water (0.43 mL), 15% NaOH (0.43 mL) and water (1.29 mL). After stirring for 15 min the mixture was filtered and evaporated to give 5-Chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzylamine (1.19 g) as a gum: 1H NMR (CDCl3, 400 MHz) δ 2.99 (m, 2H), 3.64 (m, 2H), 3.75 (s, 2H), 4.38 (d, J=5.3 Hz, 2H), 4.50 (m, 1H), 7.13 (d, J=8.0 Hz, 1H), 7.21 (dd, J=2.2, 9.7 Hz, 1H), 7.35 (d, J=2.2 Hz, 1H).

Provenance & Evidence