cis-Ethyl 2-(benzylamino)cyclopentanecarboxylate → Ethyl (1R,2S)-2-Aminocyclopentanecarboxylate

Participants

Reaction Steps

A solution of cis-ethyl 2-(benzylamino)cyclopentanecarboxylate (2.99 g, 12.1 mmol), prepared according to Bartoli, G. et al., J. Org. Chem., 59:5328-5335, was hydrogenated along with 500 mg 10% palladium on carbon in 20 mL ethanol at 45 psi for 22 h. The reaction was filtered through a 45μ filter and concentrated to give cis-ethyl 2-aminocyclopentanecarboxylate (1.75 g, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 4.14 (2H, q, J=7.13 Hz), 3.53-3.62 (1H, m), 2.75 (1H, td, J=8.37, 6.67 Hz), 1.93-2.11 (1H, m), 1.77-1.92 (3H, m), 1.43-1.62 (2H, m), 1.35 (2H, s), 1.25 (3H, t, J=7.18 Hz). MS [M+H]+=158.24.

Provenance & Evidence