Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1,2,3,6-Tetrahydropyridine | HCID 12750 | — |
| Reactant | Chloroacetyl isocyanate | HCID 78209 | — |
| Reactant | 1,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one | HCID 23121881 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23122046 | HCID 23122046 | 72.4% |
Reaction Steps
Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.22 g, 0.75 mmol) was dissolved in tetrahydrofuran (7.5 mL). 2-Chloroacetyl isocyanate (0.10 g, 0.83 mmol) was added thereto, and the mixture was stirred at −20° C. for 1 hour. 1,2,3,6-Tetrahydropyridine (0.27 mL, 3.0 mmol) was added thereto, and the mixture was stirred at room temperature for 24 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to ethyl acetate), and then crystallized from ethyl acetate-hexane to obtain the title compound (0.25 g, yield 72%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07795267B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-2663997350aa483fa83612ed199f1feb |
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| Source note | uspto-grants-2010_09 |
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