Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | ethyl 1-{2-[(tert-butoxycarbonyl)amino]propyl}-3-(phenoxymethyl)-1H-pyrazole-5-carboxylate | HCID 67958408 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67960066 | HCID 67960066 | 106.8% |
Reaction Steps
Rac-2-(2-tert-butoxycarbonylamino-propyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (5.58 g, 5.53 mmol, 40% pure) was dissolved in a 4N solution of HCl in 1,4-dioxane (40 mL) under N2 at 0° C. The mixture was stirred at room temperature for 3 hours. The mixture was basified with a saturated solution of Na2CO3 and the mixture stirred at room temperature for 3 days. Then the mixture was diluted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 70/30). The desired fractions were collected and the solvents evaporated in vacuo to yield rac-6-methyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (1.52 g, 91% yield) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09255103B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-654c5550ed6f4c969b242eb34f2b601f |
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| Source note | uspto-grants-2016_02 |
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