HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-[4-Benzyl-2-(3-hydroxybutyl)-5-pyridyl]ethynyl-3-quinuclidinol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol | HCID 3613517 | — |
| Reactant | 4-Benzyl-5-bromo-2-(3-hydroxybutyl)pyridine | HCID 18182305 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 3-[4-Benzyl-2-(3-hydroxybutyl)-5-pyridyl]ethynyl-3-quinuclidinol | HCID 18182439 | 58.1% |
Reaction Steps
50 mg of 4-benzyl-5-bromo-2-(3-hydroxybutyl)pyridine, 20 mg of 3-ethynyl-3-quinuclidinol, 20 mg of tetrakis(triphenylphosphine)palladium(0), 5 mg of cuprous iodide and 0.5 ml of triethylamine were added to 2 ml of 1-methyl-2-pyrrolidinone, followed by stirring for one hour in an oil bath kept at 110° C. After cooling as it was, it was evaporated. The residue was subjected to NH-silica gel column chromatography and eluted with 5% methanol/ethyl acetate, to give 30 mg of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06599917B1 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-6a3c561d10a44ee7aa8ad953108b2794 |
| Source note | uspto-grants-2003_07 |