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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1992366Generated: November 1, 2026

Potassium Carbonate → 7-[2-(4-Cyano-2-fluoro-phenoxy)-ethyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/1992366

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant4-(2-Bromoethoxy)-3-fluorobenzonitrileHCID 15978888—
Reactant3-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 18540412—
SolventAcetonitrileHCID 6342—
Product7-[2-(4-Cyano-2-fluoro-phenoxy)-ethyl]-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl esterHCID 6851907465.8%

Reaction Conditions

Temperature60 °C

Reaction Steps

A suspension of 4-(2-Bromo-ethoxy)-3-fluoro-benzonitrile (21.6 g, 0.0885 mol, from step (v) above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (21.1 g, 0.07965 mol; see WO 01/28992) and dry K2CO3 (48.9 g, 0.354 mol) in 200 ml of dry acetonitrile was stirred at 60° C. for five days under N2 atmosphere. The reaction mixture was filtered through celite and filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 27% ethyl acetate in petroleum ether, as eluent to yield the sub-title compound (20.5 g) as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07648985B2
Source datasetuspto-grants-2010_01
ORD IDord-e4becfefd4f944aeb1fc3ee09fcd2a88
Source noteuspto-grants-2010_01