Pyridine → HCID 57671221, compound

Participants

Reaction Steps

A solution of 2-[(pyridin-2-ylmethyl)-amino]-cyclopent-1-enecarboxylic acid ethyl ester (4.78 g, 19.4 mmol) in acetic acid (70 mL) was treated with a 8.0 M solution of borane in pyridine (2.67 mL, 21.4 mmol) and stirred under a nitrogen atmosphere for 30 min. The reaction was quenched with 1.0 M aqueous hydrochloric acid solution (40 mL) for 16 h. The reaction was then poured into a mixture of saturated aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL) and extracted. The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 0-10% methanol in dichloromethane) to afford the desired product, 2-[(pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester (3.30 g, 13.3 mmol, 68.6%), as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) δ: 1.16 (3H, t, J=7.4 Hz), 1.38-1.79 (4H, m), 1.82-1.96 (2H, m), 2.56 (1H, dd, J1=15.5 Hz, J2=7.0 Hz), 2.88 (1H, dd, J1=14.9 Hz, J2=7.1 Hz), 3.21 (1H, dd, J1=13.7 Hz, J2=6.7 Hz), 4.04 (2H, q, J=7.0 Hz), 3.78 (2H, s), 7.19-7.22 (2H, m), 7.38 (1H, d, J=7.6 Hz), 7.68-7.73 (1H, m), 8.45 (1H, d, J=4.7 Hz). LC-MS (ESI) calcd for C14H20N2O2 248.15, found 249.2 [M+H+].

Provenance & Evidence