Acetic Acid → HCID 54936468, compound

Participants

Reaction Steps

4-acetylbenzonitrile (500 mg; 3.4 mmol; 1 eq.) and tert-butyl glycinate (588 mg; 4.5 mmol) were dissolved in toluene (10 mL). AcOH (103 μl; 1.7 mmol) was added. The mixture was stirred at reflux with a dean stark trap overnight. Solvents were evaporated and the resulting tert-butyl N-[1-(4-cyanophenyl)ethylidene]glycinate (889 mg; 3.4 mmol) was dissolved in MeOH (18 mL). Sodium borohydride (390 mg; 10.3 mmol) was added in portions, resulting in an exothermic reaction (reflux). The reaction was stirred at RT overnight. Solvents were evaporated. The crude residue was suspended in EtOAc, washed with NH4Cl saturated solution, NaHCO3 saturated solution, brine and dried over MgSO4. After evaporation of the solvents the resulting yellow oil was purified by flash chromatography, affording the title compound as a colorless oil. LC/MS (Method B): 261.0 (M+H)+. HPLC (Method A): 2.77 min (purity: 98.2%).

Provenance & Evidence