HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Dioxane → HCID 68578580, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2,6-Dimethylmorpholine, cis- | HCID 641500 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | HCID 68578192 | HCID 68578192 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68578580 | HCID 68578580 | 135.9% |
Reaction Steps
A solution of tert-butyl 8-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (300 mg, 0.609 mmol), cis-2,6-dimethylmorpholine (0.370 ml, 3.00 mmol), X-phos (26.1 mg, 0.0548 mmol), tris(dibenzylideneacetone)dipalladium(0) (16.6 mg, 0.0181 mmol), sodium tert-butoxide (131 mg, 1.37 mmol) and dioxane (6 ml) was stirred under an argon atmosphere for 2 hr at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (300 mg, 90.4%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08247403B2 |
| Source dataset | uspto-grants-2012_08 |
| ORD ID | ord-c1e08a59f79146abb54cf93de9e8ee45 |
| Source note | uspto-grants-2012_08 |