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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1754313Generated: October 29, 2026

Diphosgene → (3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride

https://huagongshe.com/reaction/1754313

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiphosgeneHCID 10426—
Reactant3-Quinuclidinol, (-)-HCID 91404—
SolventAcetonitrileHCID 6342—
Product(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochlorideHCID 86676896151.9%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a stirred solution of (R)-3-quinuclidinol (2.5 g, 19.66 mmol) in acetonitrile (200 mL) was added trichloromethyl chloroformate (3.06 mL, 25.57 mmol) dropwise at 0° C., and the mixture was allowed to stir at 0° C. for 1 hour. The reaction mixture was then stirred at RT for 16 hours, and then the solvent was removed in vacuo to afford the title compound as a white solid (4.39 g, 98%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09169245B2
Source datasetuspto-grants-2015_10
ORD IDord-c2394a7a21ce4e0dbc8d20d52015f76f
Source noteuspto-grants-2015_10