HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Bis(3-fluorophenyl)methanol | HCID 2758250 | — |
| Reactant | 1-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride | HCID 12673436 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate | HCID 70925896 | 57.4% |
Reaction Steps
Quinuclidine-3-carboxylic acid hydrochloride (817 mg, 4.26 mmol), EDC (1.23 g, 6.39 mmol), and HOBT (979 mg, 6.39 mmol) were dissolved in dry DMF (40 ml). DIPEA (2.61 ml, 14.9 mmol) and bis(3-fluorophenyl)methanol (1.03 mg, 4.69 mmol) were added, and the mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted several times with Et2O. The organic phases were collected and washed with brine, dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (874 mg, racemic mixture).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08604015B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-e5b17f1598fd4752a8591a206b36f7cb |
| Source note | uspto-grants-2013_12 |