Potassium tert-butoxide → 1-[(4-Hydroxypiperidin-1-yl)carbonyl]-5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylic acid
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:27]([O:29]C)=[O:28])[CH2:11]2)=[O:9])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+]>CO>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=3)[CH2:13][CH:12]([C:27]([OH:29])=[O:28])[CH2:11]2)=[O:9])[CH2:6][CH2:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 733 mg (1.71 mmol) of the compound from Example 57A in methanol (32 ml) were added, at RT, 1.92 g (17.1 mmol) of potassium tert-butoxide. The mixture was stirred at 60° C. for 5 h. 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: 735 mg (99% of theory)
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-3664865cba944b51b0b9f0cb224433bd
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
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