Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (+-)-3-Quinuclidinol | HCID 15381 | — |
| Reactant | 2-Dibenzofuranol | HCID 66587 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ammonia | HCID 222 | — |
| Product | HCID 66838098 | HCID 66838098 | — |
Reaction Steps
To a mixture of (±)-3-quinuclidinol (3.0 g, 23.6 mmol), 2-hydroxydibenzofuran (4.3 g, 23.6 mmol), triphenylphosphine (9.29 g, 35.4 mmol) and THF, was added: diethylazodicarboxylate (6.3 ml, 35.4 mmol) over a time period of 40 min at room temperature. The mixture was stirred at 50° C. for 7 days. Aqueous sodium hydroxide (100 ml, 1 M) was added. The mixture was extracted with dichloromethane (3×100 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 2.0 g (29%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07750022B2 |
|---|
| Source dataset | uspto-grants-2010_07 |
|---|
| ORD ID | ord-efb3dd893541464cbd2436c7d9deb1e9 |
|---|
| Source note | uspto-grants-2010_07 |
|---|
