Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Phenethylamine, (+)- | HCID 643189 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | HCID 9924988 | HCID 9924988 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 69263087 | HCID 69263087 | 95.5% |
Reaction Steps
Under a nitrogen atmosphere, to toluene (10 mL) were added 5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (2 g) and (R)-(+)-1-phenylethylamine (0.94 g), then palladium acetate (5 mg) and (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-dinaphthyl (41.6 mg), and further sodium tert-botoxide (0.86 g). The mixture was stirred at 107° C. for 7 hours. Diluted hydrochloric acid was added to the reaction solution. The organic layer was separated and washed with a 10% aqueous solution of sodium chloride and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which was eluted with ethyl acetate-n-hexane [1:9], to obtain the title compound (2.12 g, 95.5%).
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-8295cc00c4ce4309899f563d3584546f |
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| Source note | uspto-grants-2006_04 |
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