Tetrahydrofuran → HCID 59861741, compound
Reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH:18]([B-](F)(F)F)=[CH2:19].[K+].C(N(CC)CC)C.O1CCCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.CO>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:18]=[CH2:19])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
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.
Workup
- temperatureThe reaction mixture was cooled back to room temperature
- extractionwas extracted with chloroform
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe insolubles were filtered
- concentrationthe filtrate was concentrated under reduced pressure
- customthe obtained residue was purified by preparative thin-layer chromatography
Sources & evidence
- ORD record
- ord-1ace8cb7b7014fd4bec3e7dfede0e17d
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718801B2
Reaction notes
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