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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1920565Generated: October 31, 2026

Quinuclidinyl benzilate, (-)- → (R)-3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(2-methylamino-ethyl)-1-azonia-bicyclo [2.2.2]octane bromide hydrobromide

https://huagongshe.com/reaction/1920565

Reaction equation

Participants

RoleNameHCIDCharge
ReactantQuinuclidinyl benzilate, (-)-HCID 688566—
ReactantHCID 53743212HCID 53743212—
SolventDimethylformamideHCID 6228—
Product(R)-3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(2-methylamino-ethyl)-1-azonia-bicyclo [2.2.2]octane bromide hydrobromideHCID 67498057—

Reaction Conditions

Temperature60 °C

Reaction Steps

(2-Bromo-ethyl)-methyl-carbamic acid tert-butyl ester (0.09 g, 0.38 mmol) is added to a solution of hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (0.265 g, 0.79 mmol) in DMF (10 ml). The resulting mixture is heated at 60° C. for 5 hours and concentrated. This procedure is repeated twice giving the title compound as a mixture containing unreacted hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08168654B2
Source datasetuspto-grants-2012_05
ORD IDord-c07ac422ef6046b9bef1567ea5c1c1b6
Source noteuspto-grants-2012_05