HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
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
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Acetonitrile | HCID 6342 | — |
| Edukt | Ethyl 5-(2-bromoacetyl)isoxazole-3-carboxylate | HCID 2736373 | — |
| Edukt | (R)-quinuclidin-3-yl 2-(benzylamino)-2-phenylacetate | HCID 46840418 | — |
| Lösungsmittel | Ethyl Acetate | HCID 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 bromide | HCID 86643228 | 35,6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08835682B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-ce6c6530706f43b8922aad771725a07f |
| Quellennotiz | uspto-grants-2014_09 |