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

HRID 654740

Reaktionsgleichung

Reaktionsgleichung von HRID 654740
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11]C)=[O:10])[CH2:2]2.[C:13](=[N:17][OH:18])([NH2:16])[CH2:14][CH3:15].[H-].[Na+].CC(O)C.ClCCl.[CH3:28][OH:29]>O1CCCC1>[C:9]([OH:11])(=[O:10])[C:28]([OH:18])=[O:29].[CH2:14]([C:13]1[N:17]=[C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N:1]([CH2:8][CH2:7]3)[CH2:2]2)[O:11][N:16]=1)[CH3:15]

Komponenten

7

Edukt 5

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 2736953Methyl quinuclidine-3-carboxylateHCID 4092053N-HydroxypropionimidamideHCID 21226129Dichloromethane methanol

Produkt 1

HCID 146855023-(3-Ethyl-1,2,4-oxadiazol-5-yl)quinuclidine Hydrogen Oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Quellen und Nachweise

ORD-Eintrag
ord-c7e60a3d7e834c0680725de526ef8f3c
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134146

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