Methyl iodide → ethyl (2S)-2-(N-methylanilino)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl N-phenylalaninate (2 g, 10.3 mmol) in DMF (103 mL) was added powdered potassium carbonate (2.6 g, 18.5 mmol) followed by iodomethane (1.03 mL, 16.6 mmol) and the resulting mixture was heated at 70° C. over 3 days. The reaction mixture was cooled to room temperature and diluted with 1 M HCl and ethyl acetate. The product was extracted 3 times with ethyl acetate and the combined organics washed with brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (8:1 hexanes/EtOAc) yielded the title compound as a colorless oil (725 mg, 34%). MS (ES+) m/z 208 (MH+).

Provenance & Evidence