Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloromethyl 2-(trimethylsilyl)ethyl ether | HCID 2724271 | — |
| Reactant | HCID 178453108 | HCID 178453108 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66853057 | HCID 66853057 | 24% |
Reaction Steps
To a solution of tert-butyl (1-benzyl-4-piperidinyl)((1H-imidazol-4-yl)methyl)carbamate (1.3 g) obtained in Example 83b) in DMF (30 ml) was added sodium hydride (0.22 g) under ice-cooling, and mixed at room temperature for 1 hour. Subsequently, 2-(trimethylsilyl)ethoxymethyl chloride (1.3 ml) was added under ice-cooling, and then mixed at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and water, and the organic layer was collected by separation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate:hexane=1:1) to obtain the title compound as a pale yellow oil (4.9 g, 24%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820673B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-4d457d30aa664d24af446df09f8b7832 |
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| Source note | uspto-grants-2010_10 |
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