Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Veratrylamine | HCID 79832 | — |
| Reactant | HCID 9924988 | HCID 9924988 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68435567 | HCID 68435567 | 64.5% |
Reaction Steps
Under a nitrogen atmosphere, to toluene (1 mL) were added 5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (100 mg) and 3,4-dimethoxybenzylamine (56 mg), then palladium acetate (0.3 mg) and (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.7 mg), and further sodium tert-butoxide (37.5 mg). The mixture was stirred at 80° C. for 17 hours. Ethyl acetate was added to the reaction mixture, insoluble materials were filtered and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which was eluted with ethyl acetate-n-hexane [1:4], to obtain the title compound (80 mg, 64.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07034166B2 |
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| Source dataset | uspto-grants-2006_04 |
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| ORD ID | ord-30d56ed473d34e5b882c7ca65f4fdcda |
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| Source note | uspto-grants-2006_04 |
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