Potassium tert-butoxide → 5-[4-(1,1-Difluoroethyl)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylic acid
Reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][N:15]([C:17]([N:19]3[CH2:24][CH2:23][S:22][CH2:21][CH2:20]3)=[O:18])[CH2:14][CH:13]([C:25]([O:27]C)=[O:26])[CH2:12]2)=[CH:7][CH:6]=1)([F:4])[CH3:3].CC(C)([O-])C.[K+]>CO>[F:4][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][N:15]([C:17]([N:19]3[CH2:24][CH2:23][S:22][CH2:21][CH2:20]3)=[O:18])[CH2:14][CH:13]([C:25]([OH:27])=[O:26])[CH2:12]2)=[CH:7][CH:6]=1)([F:1])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 528 mg (1.28 mmol) of the compound from Example 72A in 15 ml of methanol were added, at RT, 1.44 g (12.8 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: 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-c53356c935364b2eb11f81e073f8e557
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
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