Acetic Acid → 2-[2-Phenylpropylamino]ethyl carbamic acid tert-butyl ester

Participants

Reaction Steps

In the same way as that described in Example 4, Step 1, using tert-butyl-N-(2-aminoethyl)carbamate (1.6 g, 10 mmol), 2-phenylpropionaldehyde (1.32 mL, 10 mmol), MeOH (100 mL), acetic acid (1.72 mL, 30 mmol) and sodium cyanoborohydride (1.26 g, 20 mmol). The crude residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (90:10), to give the amine (1.56 g, 56%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ1.26 (3H, d, J=6.9 Hz), 1.42 (9H, s), 2.70-2.81 (4H, m), 2.90-3.00 (1H, m), 3.14-3.24 (2H, m), 4.89 (1H, br s), 7.19-7.35 (5H, m).

Provenance & Evidence