Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 77041Erstellt: 25. Oktober 2026

Acetonitrile → (R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-[2-(3-ethoxycarbonyl-isoxazol-5-yl)-2-oxo-ethyl]-1-azonia-bicyclo[2.2.2]octane bromide

https://huagongshe.com/reaction/77041

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktAcetonitrileHCID 6342—
EduktEthyl 5-(2-bromoacetyl)isoxazole-3-carboxylateHCID 2736373—
Edukt(R)-quinuclidin-3-yl 2-(benzylamino)-2-phenylacetateHCID 46840418—
LösungsmittelEthyl AcetateHCID 8857—
Produkt(R)-3-(2-benzylamino-2-phenyl-acetoxy)-1-[2-(3-ethoxycarbonyl-isoxazol-5-yl)-2-oxo-ethyl]-1-azonia-bicyclo[2.2.2]octane bromideHCID 8664322835,6%

Reaktionsschritte

Benzylamino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (C80) (100 mg, 0.28 mmol) is dissolved in ethyl acetate (1.90 mL) and acetonitrile (0.95 mL) and ethyl 5-(2-bromoacetyl)isoxazole-3-carboxylate (82.0 mg, 0.31 mmol) is added. The orange solution is stirred at RT overnight. The suspension is evaporated and the crude is purified by flash chromatography (DCM/EtOH=93/7) to obtain the title compound as a pale brown solid (61 mg, 35% yield, bromide salt, mixture of diastereoisomers).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08835682B2
Quelldatensatzuspto-grants-2014_09
ORD IDord-ce6c6530706f43b8922aad771725a07f
Quellennotizuspto-grants-2014_09