Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Reactant | HCID 66993578 | HCID 66993578 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66993408 | HCID 66993408 | 7% |
Reaction Steps
To a solution of tert-butyl 3-[(1-methylethyl)amino]-6,7-dihydropyrazino[2,3-f][1,4]oxazepine-8(9H)-carboxylate (137 mg) in tetrahydrofuran (3 mL) was added dropwise potassium hexamethyl disilazide (1.06 mL, 0.5 M toluene solution) at 0° C. The mixture was stirred at 0° C. for 15 min, and iodoethane (105 μL) was added dropwise thereto. The mixture was stirred at 0° C. for 1.5 hr, and further at room temperature overnight. Water (5 mL) was added, and the mixture was extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient: 10→40% ethyl acetate/hexane) to give the title compound (10 mg, 7%) as a pale-yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08324201B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-eaeebbf2323f40e38918c3354009f923 |
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| Source note | uspto-grants-2012_12 |
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