Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol | HCID 3613517 | — |
| Reactant | HCID 18182403 | HCID 18182403 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Chloroform methanol | HCID 21584188 | — |
| Product | HCID 18182268 | HCID 18182268 | 41% |
Reaction Steps
10 ml of N,N-dimethylformamide was added to a mixture of 1.2 g of 6-methyl-2-(2-phenylethyl)pyridyl trifluoromethane sulfonate, 522 mg of 3-ethynyl-3-quinuclidinol, 400 mg of tetrakis(triphenylphosphine)palladium(0), 217 mg of cuprous iodide and 1.7 ml of triethylamine, followed by heating under stirring at 50° C. in an oil bath for one hour in a nitrogen atmosphere. After cooling as it was, the reaction solution was sprinkled over silica gel and subjected to silica gel column chromatography using chloroform/methanol/aqueous 36% ammonia (46:5:0.5) as an eluent for separation and purification, to give 490 mg of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06599917B1 |
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| Source dataset | uspto-grants-2003_07 |
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| ORD ID | ord-da37f03d93bc474fa56b5ae646e312c0 |
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| Source note | uspto-grants-2003_07 |
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