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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 77034Generated: October 29, 2026

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

https://huagongshe.com/reaction/77034

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenacyl bromideHCID 6259—
ReactantHCID 46840706HCID 46840706—
SolventAcetonitrileHCID 6342—
Product(R)-3-[2-(3-fluoro-4-methyl-phenylamino)-2-phenyl-acetoxy]-1-(2-oxo-2-phenyl-ethyl)-1-azonia-bicyclo[2.2.2]octane bromideHCID 8664322123.2%

Reaction Steps

(R)-Quinuclidin-3-yl 2-(3-fluoro-4-methylphenylamino)-2-phenylacetate (C97) (80 mg, 0.22 mmol) and 2-bromo-1-phenylethanone (45.4 mg, 0.23 mmol) are dissolved in acetonitrile (3 mL) and stirred at RT overnight (Conversion complete by UPLC/MS). Acetonitrile is evaporated and the residue is purified by flash chromatography (DCM/MeOH=97/3) affording thetitle compound as a white solid (29 mg, 23% yield, bromide salt, mixture of diastereoisomers).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835682B2
Source datasetuspto-grants-2014_09
ORD IDord-6daa51eda9f24dbba42faaaeb1696e14
Source noteuspto-grants-2014_09