Methanol → Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate

Participants

Reaction Steps

To a 50 mL round bottom flask equipped with an electromagnetic stirrer and a drying tube, 15 mL of anhydrous methanol was added. The solution was cooled on an ice-sodium chloride bath to minus 10° C., and 2 mL of SOCl2 was added slowly. The reaction mixture was allowed to react for an hour at room temperature. Then 2.25 g of 3-amino-3-(3,4-dimethoxy-phenyl)-propionic acid (prepared according to a method disclosed in J. Med. Chem. 1996, 39, 3238) was added. The reaction mixture was allowed to react for 3 hours at room temperature, and then refluxed for 40 minutes. After the solution was evaporated to remove the solvent, 100 mL of CHCl3 and saturated NaHCO3 were added, and the layers were separated. The organic layer was washed successively with 30 mL of water and saturated brine, dried over anhydrous MgSO4, filtered, evaporated, and purified by column chromatography to give 1.9 g of oil-like products. 1H NMR (CDCl3): δ 6.77-6.88 (m, 3H), 4.34 (t, 1H, J=5 Hz), 3.85 (s, 3H), 3.82 (s, 3H), 3.64 (s, 3H), 2.61 (d, 2H, J=5 Hz), 1.83 (t, 2H, J=6 Hz)

Provenance & Evidence