Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium vinyltrifluoroborate | HCID 23679353 | — |
| Reactant | (S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate | HCID 56973617 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59861741 | HCID 59861741 | 58.7% |
Reaction Steps
The mixture of 50 mg of the t-butyl[(1S)-1-(4-bromophenyl)ethyl]carbamate [106-1], 223.4 mg of dichlorobis(triphenylphosphine)palladium (II), 31.2 mg of potassium vinyltrifluoroborate, 27.9 μL of triethylamine, 0.5 mL of tetrahydrofuran, and 0.5 mL of methanol, was stirred overnight at 100° C. The reaction mixture was cooled back to room temperature, water was added thereto, and was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by preparative thin-layer chromatography, to obtain 24.2 mg of t-butyl[(1S)-1-(4-vinylphenyl)ethyl]carbamate [152-1] as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07718801B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-1ace8cb7b7014fd4bec3e7dfede0e17d |
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| Source note | uspto-grants-2010_05 |
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