C([O-])=O.[NH4+].C([CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])C1C=CC=CC=1>C(O)C.C(O)(=O)C>[CH2:14]([NH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH3:12]Ammonium formate (2 g, 31 mmol) was added to a solution of ethyl 2-[benzylpropylamino]acetate (1.05 g, 4.47 mmol) in ethanol (15 mL) and acetic acid (1 mL). The reaction vessel was then carefully flushed with nitrogen gas. Palladium on carbon (10%, 300 mg) was added in one portion, and the resulting mixture was heated at 80° C., under nitrogen for 3 h. The reaction mixture was allowed to cool to room temperature, and filtered through celite filteraid. The filtrate was concentrated in vacuo, (azeotroping with toluene (20 mL) to remove the acetic acid), to give ethyl 2-(propylamino)acetate as a yellow oil (quantitative crude yield). 1H NMR (CDCl3) δ 4.14 (q, J=7.1 Hz, 2H), 3.30 (s, 2H), 2.60 (dd, J=7.4 Hz, 2H), 1.50 (m, 2H), 1.26 (t, J=7.2 Hz, 3H), 0.89 (t, J=7.4 Hz, 3H).
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