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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1255082Erstellt: 26. Oktober 2026

Phenacyl bromide → (R)-1-(2-oxo-2-phenyl-ethyl)-3-(2-phenyl-4-methyl-phenyl-amino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

https://huagongshe.com/reaction/1255082

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPhenacyl bromideHCID 6259—
Edukt4-methyl-phenyl-amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 86643235—
LösungsmittelAcetonitrileHCID 6342—
Produkt(R)-1-(2-oxo-2-phenyl-ethyl)-3-(2-phenyl-4-methyl-phenyl-amino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromideHCID 86643236117,3%

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

To a solution of 4-methyl-phenyl-amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (C245) (63.5 mg, 0.18 mmol) in acetonitrile (5 mL), is added 2-bromo-1-phenyl-ethanone (36 mg, 0.18 mmol) and the mixture was heated at 100° C. for 1 hour in a MW oven (UPLC-MS monitoring: complete conversion). 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 (58 mg, 32% yield, bromide salt, mixture of diastereoisomers).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08455646B2
Quelldatensatzuspto-grants-2013_06
ORD IDord-7161457187bc41ee85f30faa8c85f176
Quellennotizuspto-grants-2013_06