Acetic Acid → HCID 68433175, compound

Participants

Reaction Steps

To a solution of benzylpiperidone (5 g, 26 mmol) and (2-amino-ethyl)-carbamic acid tert-butyl ester (4.23 g, 26 mmol) and acetic acid (2.5 ml, 53 mmol) in CH2Cl2 (50.0 ml) was slowly added NaBH(OAc)3 (6.69 g, 32 mmol). On completion of the addition the reaction was stirred for 0.5 h. Saturated NaHCO3 (30 ml) was then cautiously added until the pH was basic. A solution of acrolyl chloride (2.3 ml, 29 mmol) in CH2Cl2 (10.0 ml) was then added and the reaction stirred for a further 1 h. The organic layer was then separated, dried (Na2SO4) and concentrated. The product was isolated by flash column chromatography (EtOAc) to afford the title compound as a light yellow foam (6 g, 58%). MS: 388.2 (MH+).

Provenance & Evidence