Oxalic Acid → 3-(2-Aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester ethandioate

Participants

Reaction Conditions

Reaction Steps

Alternative to the crystallization of 3-(2-Aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester from isopropyl acetate. The crude tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate (0.50 g, 0.002 mol) was dissolved in refluxing ethyl acetate (10 mL). A solution of oxalic acid (0.18 g, 0.002 mol) dissolved in ethyl acetate (5 mL) was added and produced a precipitate immediately. The resulting slurry was cooled to 0° C. and filtered. The isolated product was slurred in ethanol (5 mL), cooled to 0° C., and filtered to give 3-(2-aminomethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester ethandioate (2:1) (0.41 g, 69%). mp 188-190° C. 1H NMR (DMSO-d6): δ 1.36 (s, 18H), 2.39-2.45 (t, 4H), 2.47-2.52 (m, 4H), 2.70-2.76 (t, 4H), 3.83 (s, 4H), 6.61-6.65 (dd, 2H), 6.77-6.82 (d, 2H), 6.97-7.01 (d, 2H). MS (ES+) m/z 252.1 ([M+H]+). MS (ES−) m/z 250.2 ([M−H]−). Anal. Calculated for C30H44N2O10: C: 60.80; H: 7.48; N: 4.73. Found: C: 60.79; H: 7.51; N: 4.81.

Provenance & Evidence