Potassium tert-butoxide → 5-[3-Fluoro-4-(2,2,2-trifluoroethyl)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:19]([N:21]3[CH2:26][CH2:25][S:24][CH2:23][CH2:22]3)=[O:20])[CH2:16][CH:15]([C:27]([O:29]C)=[O:28])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]([F:12])([F:11])[F:10].CC(C)([O-])C.[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:19]([N:21]3[CH2:22][CH2:23][S:24][CH2:25][CH2:26]3)=[O:20])[CH2:16][CH:15]([C:27]([OH:29])=[O:28])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]([F:11])([F:12])[F:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 4.29 g (9.57 mmol) of the compound from Example 78A in methanol (190 ml) were added, at RT, 10.7 g (112 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: 3.94 g (76% of theory, purity 80%).
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-b583afafcea24a0fa97fea640dc1b8e6
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
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