Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 86761174 | HCID 86761174 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23122048 | HCID 23122048 | 21.4% |
Reaction Steps
To a solution of ethyl [4-[(tetrahydro-3-oxo-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-7(1H)-yl)carbonyl]piperidin-1-yl]acetate (0.13 g, 0.26 mmol) in tetrahydrofuran (3 mL) was added aluminum lithium hydride (10 mg, 0.26 mmol) at 0° C., and the mixture was stirred at 0° C. for 30 minutes. An excessive amount of ethyl acetate was added thereto, and the mixture was further stirred at 0° C. for 5 minutes. The reaction solution was diluted with water and then extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous sodium hydroxide solution, water and saturated brine, and dried over magnesium sulfate. The solid was filtered off, and the filtrate was concentrated. The residue was purified with amino silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=9:1), and then recrystallized from diisopropyl ether-ethyl acetate to obtain the title compound (25 mg, yield 21%).
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-16edd4784a20472f92b712cebaf41f86 |
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| Source note | uspto-grants-2010_09 |
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