Isopropanol → 3-(3-Ethyl-1,2,4-oxadiazol-5-yl)quinuclidine Hydrogen Oxalate

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The title compound free base (17 g, 77%) was prepared from methyl quinuclidine-3-carboxylate (18.0 g, 0.11 mol), propionamide oxime (14 g, 0.16 mol) and sodium hydride (7 g of a 55% oil dispersion, 0.16 mol) in anhydrous tetrahydrofuran (350 mL). The hydrogen oxalate salt had mp 113°-115° C. (propan-2-ol). Rf 0.3 in dichloromethane/methanol (50:1) on alumina plates. (Found: C, 52.25; H, 6.41; N, 14.07. C11H17N3O.C2H2O4 requires C, 52.52; H, 6.44; N, 14.13%).

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