To a solvent mixture of methanol (30 mL) and tetrahydrofuran (30 mL) was added 10% Pd/C catalyst (400 mg) as methyl (E)-3-(4-nitrophenyl)acrylate (S31, 4.10 g, 19.8 mmol). The reaction mixture was purged with hydrogen and then the reaction was stirred at 25°C for 10 hours. Upon completion of the reaction, the suspension was filtered through diatomaceous earth and the filtrate was concentrated to give the yellow solid product methyl 3-(4-aminophenyl)propionate (S32, 3.40 g, 19.0 mmol, 95% yield). The structure of the product was determined by 1H NMR (CDCl3, 500 MHz) δ 6.99 (d, 2H, J = 8.2 Hz), 6.63 (d, 2H, J = 8.4 Hz), 3.60 (s, 3H), 2.85 (t, 2H, J = 7.7 Hz), 2.58 (t, 2H, J = 7.7 Hz); 13C NMR (CDCl3, 125 MHz) δ 173.5, 144.6, 130.5, 129.1, 115.3, 51.5, 36.1, 30.1 confirmed.
