Triethylamine → 3-{3-[(4-Isobutyl-benzylamino)-methyl]-phenyl}-propionic acid methyl ester

Participants

Reaction Steps

A solution of 3-(3-aminomethyl-phenyl)-propionic acid methyl ester hydrochloride salt (400 mg, 1.74 mmol), 4-isobutylbenzaldehyde (311 mg, 1.91 mmol), and triethylamine (0.26 mL, 1.91 mmol) in CH2Cl2 (4 mL) was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (590 mg, 2.78 mmol) was added and the reaction was stirred for 20 h. Aqueous NaHCO3 was added and the aqueous solution was washed with CH2Cl2. The organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (65% EtOAc in hexanes) provided the title compound of Step A (178 mg). 1H NMR (400 MHz, CDCl3) δ 7.26-7.04 (m, 8H), 3.77 (s, 2H), 3.75 (s, 2H), 3.63 (s, 3H), 2.91 (t, 2H), 2.60 (t, 2H), 2.41 (d, 2H), 1.80 (m, 1H), 0.85 (m, 6H); MS 340 (M+1).

Provenance & Evidence