Tetrabutylammonium Fluoride → 2-Ethenylpiperidin-4-one
Reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5](C(OCC[Si](C)(C)C)=O)[CH:4]([CH:17]=[CH2:18])[CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH:17]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:7][CH2:6][NH:5]1)=[CH2:18]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(trimethylsilyl)ethyl 4-oxo-2-vinylpiperidine-1-carboxylate (24.1 g, 89.0 mmol) was dissolved in tetrahydrofuran (90 ml) at 0° C. and added TBAF (268 ml, 268 mmol) dropwise. The solution stirred at 0° C. for 30 min then at rt for an additional three hrs. The solution was quenched with 1N HCl and extracted five times with EtOAc. The organic fractions were combined, dried with Na2SO4, and concentrated. The crude product was not purified.
Workup
- waitat rt for an additional three hrs
- customThe solution was quenched with 1N HCl
- extractionextracted five times with EtOAc
- dry with materialdried with Na2SO4
- concentrationconcentrated
- customThe crude product was not purified
Sources & evidence
- ORD record
- ord-fbf73bb80b2548a88a9662d0c6031966
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211904B2
Reaction notes
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