Acetic Acid → HCID 66652745, compound

Participants

Reaction Steps

A solution of 4-(2-methoxyacetoyl)benzonitrile (0.338 g; 1.93 mmol) and glycine tert-butyl ester (0.382 mg; 2.90 mmol) in DCM/MeOH (1:1; 10 mL) was stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (0.182 g; 2.90 mmol) and acetic acid (0.166 mL; 2.90 mmol) were added to the reaction mixture and the mixture stirred for 18 hours. Aqueous paraformaldehyde (0.787 mL) and sodium cyanoborohydride (0.182 g; 2.90 mmol) were added and the reaction mixture stirred for a further 72 hours. The reaction mixture was diluted with DCM and water and then poured through a hydrophobic frit. The filtrate was evaporated in vacuo. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (3:2) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.62-7.61 (m, 2H), 7.51-7.49 (m, 2H), 4.09-4.06 (m, 1H), 3.62 (m, 2H), 3.42-3.37 (m, 1H), 3.29 (s, 3H), 3.21-3.17 (m, 1H), 2.39 (s, 3H), 1.47 (s, 9H).

Provenance & Evidence