Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Dithionite | HCID 24489 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 131732765 | HCID 131732765 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 131732766 | HCID 131732766 | — |
Reaction Steps
Di-t-butyl (4-cyano-2-methyl-6-nitrophenyl)imidodicarbonate obtained in Step 1 (3.77 g, 10 mmol) was dissolved in THF (0.2 M, 50 mL), and a solution prepared by dissolving sodium hydrosulfite (15.7 g, 9 eq, 90 mmol) and sodium bicarbonate (7.56 g, 90 mmol) in H2O (0.1 M, 100 mL) was added thereto. Subsequently, MeOH (17 mL) was added to the mixture, which was then stirred at room temperature for 1 hour. Upon completion of the reaction, THF and MeOH were removed under reduced pressure, and the residue was added with brine and extracted with ethyl acetate. The organic layer thus obtained was dried over MgSO4 and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (EA:Hex=1:2) to obtain the title compound in a white solid (2.90 g, yield: 83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09018233B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-6196e78a8e524f0192fae99cad5c0177 |
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| Source note | uspto-grants-2015_04 |
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