Triethylamine → 1-Aminomethyl-2-isobutyl-cyclopropanecarboxylic acid ethyl ester

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Reaction Steps

To a solution of 1-cyano-2-isobutyl-cyclopropanecarboxylic acid ethyl ester (0.41 g, 2.10 mmol) in 45 mL EtOH was added triethylamine (5.0 mL) and Raney nickel (1.0 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 18 hours, filtered, and concentrated. Flash chromatography of the residue (5→10% MeOH/CH2Cl2) provided 0.11 g (26%) of 1-aminomethyl-2-isobutyl-cyclopropanecarboxylic acid ethyl ester as a colorless oil. 1H NMR δ 4.10 (q, J=7.1 Hz, 2H), 2.90 (d, J=14.2 Hz, 1H), 2.76 (d, J=14.2 Hz, 1H), 1.63 (m, 1H), 1.52 (m, 2H), 1.34 (m, 1H), 1.22 (t, J=7.1 Hz, 3H), 1.04 (m, 1H), 0.90 (m, 6H), 0.49 (m, 1H). 13C NMR δ 175.51, 60.75, 42.42, 37.92, 30.61, 29.04, 26.46, 22.91, 22.63, 21.31, 14.49.

Provenance & Evidence