Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Cyclobutanone | HCID 14496 | — |
| Reactant | HCID 67959348 | HCID 67959348 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 67959083 | HCID 67959083 | 58.5% |
Reaction Steps
To a solution of tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (334 mg) obtained in Example 1, steps 1-3, and Et2O (10 mL) was added dropwise 1.6 N hexane solution of n-butyllithium (72.4 ml) at −78° C., and the mixture was stirred at −78° C. for 15 min. Cyclobutanone (0.0747 ml) was added, and the mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added water (10 mL), and the organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane) to give the title compound (190 mg, 58.5%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08916549B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-c17957dc14ba45e7a39d29fb35a93c9c |
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| Source note | uspto-grants-2014_12 |
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