Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Potassium vinyltrifluoroborate | HCID 23679353 | — |
| Reactant | (S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate | HCID 56973617 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59861741 | HCID 59861741 | 58.9% |
Reaction Steps
A mixture of 1.0 g of the compound [1-1], 892 mg of potassium vinyltrifluoroborate, 468 mg of dichlorobis(triphenylphosphine) palladium (II), 10 mL of 2.0M aqueous sodium carbonate solution, and 20 mL of N,N-dimethylformamide, was stirred overnight at 90° C. After standing to cool, water was added to the reaction solution, which was extracted with ethyl acetate. The resulting 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 resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-75/25), to obtain 485 mg of tert-butyl[(1S)-1-(4-vinylphenyl)ethyl]carbamate [5-1] (hereinafter, referred to as the compound [5-1]) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977336B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-9079e212e9cb4974ac0421f6079d8716 |
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| Source note | uspto-grants-2011_07 |
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