HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → HCID 86688888, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 3-Quinuclidinol, (-)- | HCID 91404 | — |
| Reactant | HCID 16192951 | HCID 16192951 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86688888 | HCID 86688888 | 43.5% |
Reaction Steps
2-(4-Methylpiperidin-1-yl)-2-phenylacetic acid hydrochloride (105 mg, 0.39 mmol), HOBT (119 mg, 0.78 mmol), and DCC (161 mg, 0.78 mmol) were dissolved in dry THF (5 ml). (R)-quinuclidin-3-ol (149 mg, 1.17 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. THF was evaporated, the residue was dissolved in EtOAc and washed with sat. NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(4-methylpiperidin-1-yl)-2-phenylacetate (58 mg, 43.5% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748613B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-da4ad630604d460db2ffe7596faa0400 |
| Source note | uspto-grants-2014_06 |