Reacción #2175492

Ecuación de reacción

2-Chloro-1-methyl pyridinium iodide

(S)-(−)-3-Aminoquinuclidine dihydrochloride

o-Methoxybenzoic acid

Triethylamine

→

(S)-2-methoxy-N-(quinuclidin-3-yl)benzamide

Rendimiento 85.0%

Disolventes

water

Acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas subsequently injected into a Preparative HPLC instrument for purification
2. 2
   Concentraciónconcentrated under vacuum

Procedimiento

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 o-Methoxybenzoic acid (167 mg, 1.1 mmol), followed by addition of 2-Chloro-1-methyl pyridinium 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)-2-methoxy-N-(quinuclidin-3-yl)benzamide (221 mg, 85% yield) was isolated as an oil. 1H NMR (400 MHz, Methanol-D4) δ (ppm): 7.79 (dd, J=7.7 1.6 Hz, 1H), 7.51 (td, J=8.0, 1.6 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 7.06 (t, J=7.4 Hz, 1H), 4.45 (m, 4H), 3.97 (s, 3H), 3.82 (ddd, J=11.7, 9.9, 2.0 Hz 1H), 3.37 (m, 4H), 2.37 (q, J=3.2 Hz, 1H), 2.20 (m, 1H), 2.09 (m, 2H), 1.99 (m, 1H). LCMS (ESI): m/z 261.1 (M+H [C15H20N2O]=261.15).

Fuente