HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (2S,4S)-1-[[(4-carbamoylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile | HCID 21090395 | — |
| Reactant | 4-Aminobicyclo[2.2.2]octane-1-carboxamide | HCID 23150530 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (2S,4S)-1-[[(4-carbamoylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile | HCID 11336237 | 98.2% |
Reaction Steps
4-Aminobicyclo[2.2.2]octane-1-carboxamide (50.0 mg) was dissolved in N,N-dimethylformamide (2 mL). To this solution, potassium carbonate (50.0 mg) was added, followed by dropwise addition of (2S,4S)-1-(2-bromoacetyl)-4-fluoropyrrolidine-2-carbonitrile (70.0 mg) in N,N-dimethylformamide (1 mL) at room temperature. The mixture was stirred at room temperature for 2.5 hours and was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluant:chloroform:methanol=10:1) to give (2S,4S)-1-[[(4-carbamoylbicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (94.1 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07560569B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-95e9291a90e644beb6ef72805a99c3ad |
| Source note | uspto-grants-2009_07 |