HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-Bromo-2',4'-difluoroacetophenone → (R)-1-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl]-3-(2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 2-Bromo-2',4'-difluoroacetophenone | HCID 2774185 | — |
| Edukt | (R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate | HCID 46840261 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Produkt | (R)-1-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl]-3-(2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide | HCID 46842122 | 44% |
Reaktionsschritte
To a solution of (R)-phenyl-phenylamino-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Diastereoisomer 1 of C2) (50 mg, 0.15 mmol) in acetonitrile (1 mL), is added 2-bromo-1-(2,4-difluoro-phenyl)-ethanone (35 mg, 0.15 mmol) and the mixture reacted in a closed vessel under MW irradiation for 1 hour at 100° C. (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the resulting crude is purified by flash chromatography (DCM/MeOH=95/5) to obtain the title compound as a white solid (37.3 mg, 44% yield, bromide salt, single diastereoisomer).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08835682B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-79b62d83923b4c42b9f8a81a4900c86b |
| Quellennotiz | uspto-grants-2014_09 |