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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1596463Generated: October 25, 2026

Potassium Carbonate → 1-Cyano-1-methylethyl 7-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

https://huagongshe.com/reaction/1596463

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant1-Cyano-1-methylethyl chloroformateHCID 5325480—
Reactant4-[3-(3,7-Diazabicyclo[3.3.1]non-3-yl)-2-hydroxypropoxy]benzonitrileHCID 21701946—
SolventAcetonitrileHCID 6342—
Product1-Cyano-1-methylethyl 7-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateHCID 5434423359%

Reaction Conditions

Temperature40 °C

Reaction Steps

1-Cyano-1-methylethyl chloroformate (0.4 g; 1.65 mmol; from step (a) above) was added to a stirred solution of 4-[3-(3,7-diazabicyclo[3.3.1]non-3-yl)-2-hydroxypropoxy]benzonitrile (0.5 g; 1.65 mmol; see Example G above) and K2CO3 (0.7 g) in MeCN (25 mL). The reaction mixture was stirred at 40° C. for 2 h. The salts were filtered off and the filtrate was concentrated and subjected to column chromatography (DCM:MeOH; 19:1) to give the title compound in a 59% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06291475B1
Source datasetuspto-grants-2001_09
ORD IDord-8a1458b386d24cd3926f094d9ee24c91
Source noteuspto-grants-2001_09