1-Cyano-2,2-dipropyl-cyclopropanecarboxylic acid benzyl ester → 1-Aminomethyl-2,2-dipropyl-cyclopropanecarboxylic acid

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Reaction Steps

To a solution of 1-cyano-2,2-dipropyl-cyclopropanecarboxylic acid benzyl ester (0.35 g, 1.79 mmol) in 16 mL MeOH—HCl was added platinum dioxide (PtO2) (0.035 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 21 hours. The mixture was filtered and concentrated. Flash chromatography of the residue on silica gel (0.25:1.25:3.5 conc. ammonium hydroxide (NH4OH) (aq):MeOH:CH2Cl2), followed by ion-exchange chromatography on a DOWEX-50WX8-100 resin provided 0.09 g (18%) of 1-aminomethyl-2,2-dipropyl-cyclopropanecarboxylic acid as a colorless solid, mp 255–257° C.: 1H NMR (CD3OD) δ 3.26 (d, J=12.9 Hz, 1H), 3.03 (d, J=12.9 Hz, 1H), 1.69 (m, 1H), 1.56 (m, 2H), 1.28–1.50 (m, 4H), 1.26 (d, J=4.4 Hz, 1H), 1.17 (m, 1H), 0.93 (t, J=7.3 Hz, 3H), 0.85 (t, J=7.3 Hz, 3H), 0.54 (d, J=4.6 Hz, 1H). LRMS: m/z 198.1 (M−1). Anal. Calcd for C11H21NO2: C, 66.29; H, 10.62; N, 7.03. Found: C, 66.39; H, 10.79; N, 7.05.

Provenance & Evidence