Potassium tert-butoxide → 5-[4-(1,1-Difluoroethyl)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylic acid
Reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][N:21]([C:23]([N:25]3[CH2:30][CH2:29][S:28][CH2:27][CH2:26]3)=[O:24])[CH2:20][CH:19]([C:31]([O:33]C)=[O:32])[CH2:18]2)=[CH:13][CH:12]=1)([F:10])[CH3:9]>CO>[F:10][C:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][N:21]([C:23]([N:25]3[CH2:30][CH2:29][S:28][CH2:27][CH2:26]3)=[O:24])[CH2:20][CH:19]([C:31]([OH:33])=[O:32])[CH2:18]2)=[CH:13][CH:12]=1)([F:7])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
1.44 g (12.8 mmol) of potassium tert-butoxide were added at RT to a solution of 528 mg (1.28 mmol) of the compound from Example 52A in 15 ml of methanol. 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: 471 mg (91% of theory, 2:1 cis/trans isomer mixture)
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-0bd7a13cc9254a64b63aa83781d3b7c2
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440657B2
Reaction notes
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