Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 22632373 | HCID 22632373 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 22632504 | HCID 22632504 | — |
Reaction Steps
2.04 g (7.8 mmol) of methyl 1-benzyl-4-nitro-1H-pyrazole-3-carboxylate was dissolved in a mixture of 10 ml of ethanol, 10 ml of THF and 5 ml of 1 N sodium hydroxide, and the obtained solution was stirred at room temperature for 4 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated, and the obtained crude product was dissolved in 100 ml of THF. 1.5 ml (10.1 mmol) of triethylamine and 0.81 ml (8.5 mmol) of ethyl chloroformate were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 30 minutes. Apiece of ice and 600 mg (15.6 mmol) of sodium borohydride were added to the obtained mixture. The temperature was elevated to room temperature, and the obtained mixture was stirred overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the crude product was obtained. After the purification by the silica gel column chromatography, the title compound was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06825191B2 |
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| Source dataset | uspto-grants-2004_11 |
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| ORD ID | ord-8b3d1411c48c4bb4a39dc1d795ec1cd5 |
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| Source note | uspto-grants-2004_11 |
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