Potassium Carbonate → 4-(2-Formyl-4-trifluoromethyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:5].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24](OS(C)(=O)=O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([O:1][C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-hydroxy-5-trifluoromethyl-benzaldehyde (1.36 g, 7.17 mmol), 4-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester (2.2 g, 7.88 mmol) and K2CO3 (2.96 g, 21.5 mmol) in anhydrous N,N-dimethylformamide (15 mL) was heated at 100° C. for 1 h. After cooled to room temperature, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in DCM (50 mL). The solution was washed with water, dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography to give the title compound (1.43 g).
Workup
- temperatureAfter cooled to room temperature
- filtrationthe mixture was filtered
- concentrationthe filtrate was concentrated
- dissolutionThe residue was dissolved in DCM (50 mL)
- washThe solution was washed with water
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-a80e9f09da274a6087cf62255ea6dc59
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08134001B2
Reaction notes
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