Acetic Acid → HCID 66652938, compound

Participants

Reaction Conditions

Reaction Steps

4-Acetylbenzonitrile (1.0 g; 6.9 mmol) and tert-butyl glycinate (1.2 g; 9.0 mmol) were dissolved in toluene (20 mL). The mixture was stirred at reflux with a Dean-Stark trap. AcOH (207 μL; 3.4 mmol) was added and the mixture was further heated overnight. Solvents were evaporated. The crude was dissolved in MeOH (35 mL). The solution was cooled down to 0° C. and sodium borohydride (781 mg; 21 mmol) was added in portions. The reaction was stirred at 0° C. for 1 h and was let 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 716 mg as a colorless oil. LC/MS (Method B): 261.0 (M+H)+. HPLC (Method A) Rt 2.79 min (Purity: 99.2%).

Provenance & Evidence