Water → Ethyl 2-oxo-3-(3,4,5-trifluorophenoxy)piperidine-3-carboxylate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:24].O>CN(C=O)C.[Cl-].[Na+].O>[O:24]=[C:19]1[C:18]([O:10][C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=2)([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:22][CH2:21][NH:20]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of 3,4,5-trifluorophenol (14.4 g) and potassium carbonate (40.3 g) in DMF (200 mL) was added ethyl 3-chloro-2-oxopiperidine-3-carboxylate (20 g), and the mixture was stirred at 100° C. for 1 hr. To the reaction mixture were added water (200 mL) and saturated brine (200 mL) at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL) and saturated brine (200 mL×2), and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (24.61 g).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL) and saturated brine (200 mL×2)
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-106c5625101a4a4f9382f4921d49f5df
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822699B2
Reaction notes
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