Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | HCID 66609320 | HCID 66609320 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66609159 | HCID 66609159 | 84.5% |
Reaction Steps
Phosphorus oxychloride (9.3 mL, 99.9 mmol) was added to a stirred solution of 3-oxo-4-(2-phenoxy-acetylamino)-piperidine-1-carboxylic acid ethyl ester (30.3 g, 90.8 mmol) in 1,4-dioxane (454 mL). The mixture was stirred at 100° C. for 2 hours. The mixture was cooled at 0° C., treated with water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The product was purified by flash column chromatography (AcOEt in DCM 0/100 to 30/70). The desired fractions were collected and evaporated in vacuo to yield 2-phenoxymethyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (23.2 g, 84% yield) as a colourless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09090632B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-9c4fcfd3541d44b481a977483dd434d0 |
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| Source note | uspto-grants-2015_07 |
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