Potassium tert-butoxide → 1-(Thiomorpholin-4-ylcarbonyl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylic acid
Reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][CH:11]([C:26]([O:28]C)=[O:27])[CH2:10]2)=[O:8])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+]>CO>[N:1]1([C:7]([N:9]2[CH2:14][CH:13]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][C:22]([F:24])([F:25])[F:23])=[CH:19][CH:20]=3)[CH2:12][CH:11]([C:26]([OH:28])=[O:27])[CH2:10]2)=[O:8])[CH2:2][CH2:3][S:4][CH2:5][CH2:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2.97 g (6.90 mmol) of the compound from Example 55A in methanol (83 ml) were added, at RT, 7.74 g (69.0 mmol) of potassium tert-butoxide. The mixture was stirred at 60° C. overnight. For workup, the methanol was removed under reduced pressure, and the residue was admixed with water and acidified (pH=1) with aqueous 1 N hydrochloric acid solution. The mixture was extracted with ethyl acetate, and the organic phase was dried with magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 2.61 g (76% of theory, purity 84%)
Workup
- customFor workup, the methanol was removed under reduced pressure
- extractionThe mixture was extracted with ethyl acetate
- dry with materialthe organic phase was dried with magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-303d793d094b4372b890c9c42af4e8e9
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
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