Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopentanol | HCID 7298 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | HCID 12051151 | HCID 12051151 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 15895873 | HCID 15895873 | 71.9% |
Reaction Steps
Cyclopentanol (0.11 g, 1.3 mmol) and triphenylphosphine (0.47 g, 1.8 mmol) are dissolved in THF (15 ml), and thereto are successively add with stirring diisopropyl azodicarboxylate (0.26 g, 1.3 mmol) and 2-(3-hydroxyphenylthio)-3-[3-(pyridin-4-yl)propoxy]pyridine (0.30 g, 0.89 mmol) obtained in Example 13. The mixture is further stirred at room temperature for 30 minutes, and the reaction solution is concentrated under reduced pressure. The residue is extracted with a 10% aqueous hydrochloric acid solution (30 ml), and the aqueous layer is washed with chloroform (30 ml×2), and the pH value thereof is adjusted to pH 12 with potassium carbonate. The mixture is extracted with ethyl acetate (50 ml×2), and the organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform/methanol) to give the title compound (0.26 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06765095B2 |
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| Source dataset | uspto-grants-2004_07 |
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| ORD ID | ord-e2e10fdc8061457c994c7c2c310fe0b4 |
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| Source note | uspto-grants-2004_07 |
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