Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | N-Methyl dicyclohexylamine | HCID 24210 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | N-(tert-Butoxycarbonyl)-3-bromoaniline | HCID 2757254 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 131730651 | HCID 131730651 | 911.6% |
Reaction Steps
Tris(dibenzylideneacetone)dipalladium (0.10 g, 0.00011 mol) and tri-tert-butylphosphonium tetrafluoroborate (0.064 g, 0.00022 mol) in a flask was evacuated and refilled with N2 (3 times). Then 1,4-dioxane (7.0 mL) was added followed by consecutive addition of tert-butyl (3-bromophenyl)carbamate (2.00 g, 0.00735 mol), 2-propen-1-ol (0.854 g, 0.0147 mol), N-cyclohexyl-N-methyl-cyclohexanamine (1.7 g, 0.0088 mol). The reaction mixture was stirred at 40° C. overnight, filtered, and washed with dichloromethane. The filtrate was concentrated and purified by chromatography on silica gel with 40% EtOAc in hexanes to afford the desired product (0.5 g, 30%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08461330B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-075f8a4ab782479b8ae393550cddf940 |
|---|
| Source note | uspto-grants-2013_06 |
|---|
