Potassium tert-butoxide → 1-(Thiomorpholin-4-ylcarbonyl)-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylic acid
Reaction equation
CC(C)([O-])C.[K+].[N:7]1([C:13]([N:15]2[CH2:20][CH:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[CH2:18][CH:17]([C:32]([O:34]C)=[O:33])[CH2:16]2)=[O:14])[CH2:12][CH2:11][S:10][CH2:9][CH2:8]1>CO>[N:7]1([C:13]([N:15]2[CH2:20][CH:19]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][C:28]([F:30])([F:31])[F:29])=[CH:25][CH:26]=3)[CH2:18][CH:17]([C:32]([OH:34])=[O:33])[CH2:16]2)=[O:14])[CH2:8][CH2:9][S:10][CH2:11][CH2:12]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
7.74 g (69.0 mmol) of potassium tert-butoxide were added at RT to a solution of 2.97 g (6.90 mmol) of the compound from Example 44A in methanol (83 ml). The mixture was stirred at 60° C. overnight. For workup, the methanol was removed under reduced pressure, the residue was admixed with water and the mixture was 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-cb8e0bb9944f4972b8b1f9aa4d50366f
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440657B2
Reaction notes
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