Fusaric Acid → HCID 45381411, compound

Participants

Reaction Steps

1.5 ml of Acetonitrile and Triethylamine (700 uL, 5.0 mmol) was added to a flask charged with (S)-(−)-3-Aminoquinuclidine dihydrochloride (199 mg, 1.0 mmol) and Fusaric acid (197 mg, 1.1 mmol), followed by addition of 2-Chloro-1-methylpyridinium iodide (383 mg, 1.5 mmol) at room temperature. After stirring overnight, about 2 ml of water was added to reaction mixture to resolve a clear solution that was subsequently injected into a Preparative HPLC instrument for purification. Desired fractions were combined and concentrated under vacuum. (S)-5-butyl-N-(quinuclidin-3-yl)pyridine-2-carboxamide (273 mg, 95% yield) was isolated as clear brown colored oil. 1H NMR (400 MHz, Methanol-D4) δ (ppm): 8.52 (d, J=1.8 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.84 (dd, J=8.0 Hz, 1H), 4.50 (m, 1H), 3.82 (ddd, J=10.0, 3.0, 2.6 Hz, 1H), 3.49 (m, 1H), 3.37 (m, 3H), 2.76 (t, J=7.8 Hz, 2H), 2.38 (m, J=3.1 Hz, 1H), 2.26 (m, 1H), 2.12 (td, J=8.0, 3.1 Hz 2H), 1.96 (m, 1H), 1.68 (m, J=7.7 Hz, 2H), 1.40 (m, J=4.5 Hz, 2H), 0.97 (t, J=7.4 Hz, 3H). LCMS (ESI): m/z 288.1 (M+H [C17H25N3O]=288.20).

Provenance & Evidence