Water → 2-Oxo-4-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[Na].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[OH2:19]>C(OCC)(=O)C.[Ru]=O>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:16])[F:17])[CH2:11][C:10]1=[O:19])=[O:8])([CH3:5])([CH3:3])[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
2.82 g (3.2 mmol) of sodium methaperiodate (NaIO4) was dissolved in 20 mL of water, followed by addition of 117 mg (0.88 mmol) of ruthenium oxide (RuO2). To The reaction, was added a solution in which 660 mg (2.6 mmol) of 4-trifluoromethyl-piperidin-1-carboxylic acid t-butyl ester dissolved in 35 mL of ethyl acetate, followed by stirring for 2 hours and 20 minutes. The reaction solution was diluted with excess ethylacetate and washed once with water and aqueous NaCl, respectively, and then dried over anhydrous magnesium sulfate and filtered off. The filtrated solution was distilled off under reduced pressure, then the residue was purified by column chromatography (2:1 hexane:ethyl acetate) to give 0.63 g of the title compound in a yield of 90%.
Workup
- customTo The reaction
- washwashed once with water and aqueous NaCl
- dry with materialrespectively, and then dried over anhydrous magnesium sulfate
- filtrationfiltered off
- distillationThe filtrated solution was distilled off under reduced pressure
- customthe residue was purified by column chromatography (2:1 hexane:ethyl acetate)
Sources & evidence
- ORD record
- ord-afe85805d0e34822b87683244d9466e8
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879848B2
Reaction notes
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