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

Participants

Reaction Conditions

Reaction Steps

To 150 mL of stirred methanol at 0° C. under nitrogen was slowly added thionyl chloride (14.2 mL, 194.4 mmol). To the reaction mixture was then added 3-amino-3-(3,4-dimethoxyphenyl)propionic acid (15.5 g, 64.8 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature, and stirred overnight. The reaction solution was concentrated to an oil and then diluted with 200 mL of CH3OH/Et2O (1/3) and stirred. The resulting slurry was filtered and the solid was washed with a copious amount of ether. The solid was dried in vacuo (60° C., <1 mm) to afford 1.83 g (66%) of methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride as a white powder: 1H NMR (DMSO-6, 250 MHz) δ8.59 (br s, 3H, NH3), 6.9-7.3 (m, 3H, Ar), 4.52 (overlapping dd, 1H), 3.77 (s, 3H, OCH3), 3.75 (s, 3H, OCH3), 3.67 (s, 3H, OCH3), 3.16 (dd, 1H, J1 =6 Hz, J2 =16 Hz), 2.98 (dd, 1H, J1 =8 Hz. J2 =16 Hz); 13C NMR (DMSO-d6) δ169.6, 149.0, 129.0, 120.0, 111.5, 111.4, 55.7, 55.5, 51.7, 50.8, 38.5. Anal. Calcd for C12 H18NO4Cl. Theoretical C, 52.27; H, 6.58; N, 5.08. Found C, 52.44; H, 6.53; N, 5.01.

Provenance & Evidence