Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | (5-(Benzyloxy)pyridin-2-yl)methanol | HCID 11736050 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23130583 | HCID 23130583 | — |
Reaction Steps
To a solution of (5-benzyloxy-pyridin-2-yl)-methanol described in Preparation Example 183 (2.00 g, 9.29 mmol) in tetrahydrofuran (40 mL) were added phthalimide (1.50 g, 10.2 mmol), triphenylphosphine (2.92 g, 11.1 mmol) and diethyl azodicarboxylate (5.08 mL, 11.1 mmol, 40% toluene solution) at 0° C., and the solution was stirred at room temperature for 2 hours. The reaction solution was partitioned in water and ethyl acetate. The organic layer was separated, washed with brine and dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1), and the title compound (4.1 g, quantitatively) was obtained as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932272B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-4f4358e9f67644e09f8ed5029c5ee90b |
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| Source note | uspto-grants-2011_04 |
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