Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | HCID 69067548 | HCID 69067548 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69072025 | HCID 69072025 | 100.2% |
Reaction Steps
A solution of (6R*,7S*,9aR*)-7-hydroxy-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one (164 mg), TBSCl (165 mg), imidazole (149 mg), and DMAP (6.7 mg) in DMF (5.0 mL) was stirred at room temperature overnight. To make the starting material disappear, TBSCl (165 mg) was added to the reaction solution, which was then stirred at room temperature overnight. Water 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 (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 227 mg of the title compound. The property values of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08048878B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-e76697924cc7402ca58eeccfbd237c7a |
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| Source note | uspto-grants-2011_11 |
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