HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → HCID 18182208, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol | HCID 3613517 | — |
| Reactant | HCID 18182218 | HCID 18182218 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18182208 | HCID 18182208 | 99.7% |
Reaction Steps
A mixture of 220 mg of 2-benzyl-7-ethoxycarbonyl-3-quinolyl Trifluoromethane sulfonate, 83 mg of 3-ethynyl-3-quinuclidinol, 116 mg of tetrakis(triphenylphosphine)palladium(0), 19 mg of cuprous iodide, 209 μl of triethylamine and 5.0 ml of N,N-dimethylformamide was stirred at room temperature for 45 minutes in a nitrogen atmosphere. The reaction solution was poured into aqueous dilute ammonia, followed by extracting with ethyl acetate. Then, the organic phase was washed with brine and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) chromatography and eluted with hexane/ethyl acetate (1:1) and then with ethyl acetate/methanol (15:1), to give 220 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-5cee24e9d352422b88dd96d08acfd096 |
| Source note | uspto-grants-2003_07 |