Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Di-tert-butyl diazene-1,2-dicarboxylate | HCID 6034084 | — |
| Reactant | HCID 59226486 | HCID 59226486 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59226503 | HCID 59226503 | 63% |
Reaction Steps
To a solution of 3-(3-nitropyridin-4-yl)cyclohex-2-enol (1.0 equiv.), triphenylphosphine (1.5 equiv.) and phthalimide (1.5 equiv.) in THF (0.3 M) at 0° C. was added (E)-di-tert-butyl diazene-1,2-dicarboxylate (1.5 equiv.) dropwise. The reaction was stirred at 0° C. for 2 hours. Concentrated to dryness under vacuo, then purified the crude via silica gel column chromatography eluting with EtOAc and hexanes (1:1 with 5% methanol) to afford the 2-(3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (63% yield). LC/MS=350.3 (M+H), LC=3.936 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592455B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-246ba64a62444f71947e779074660751 |
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| Source note | uspto-grants-2013_11 |
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