Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 69077725 | HCID 69077725 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 24781611 | HCID 24781611 | 70.8% |
Reaction Steps
TBAF (1.0 M solution in THF, 144 μL) was added to a solution of (E)-(6S*,8S*,9aR*)-8-(tert-butydimethylsilanyloxy)-6-(3,4,5-trifluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one (44.1 mg) in THF (1.0 mL), and the reaction solution was stirred at room temperature overnight. A saturated ammonium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 25.4 mg of the title compound. The property values of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08048878B2 |
|---|
| Source dataset | uspto-grants-2011_11 |
|---|
| ORD ID | ord-b54e0038ba4345fa978e42ee68f5ab0f |
|---|
| Source note | uspto-grants-2011_11 |
|---|