Potassium tert-butoxide → 1-(tert-Butoxycarbonyl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine-3-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][CH:15]([C:26]([O:28]C)=[O:27])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].CC(C)([O-])C.[K+]>CO>[C:22]([O:21][C:19]([N:17]1[CH2:18][CH:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:11])([F:10])[F:12])=[C:2]([F:1])[CH:3]=2)[CH2:14][CH:15]([C:26]([OH:28])=[O:27])[CH2:16]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3.72 g (8.82 mmol) of 1-tert-butyl 3-methyl 5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate were dissolved in 65 ml of methanol and admixed at RT with 9.90 g (88.2 mmol) of potassium tert-butoxide. After a reaction time of 19 hours, the mixture was concentrated under reduced pressure, taken up in 50 ml of water and adjusted to pH=5 with 1 N hydrochloric acid. The aqueous phase was extracted three times with 50 ml each time of ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 3.11 g (85% of theory)
Workup
- concentrationAfter a reaction time of 19 hours, the mixture was concentrated under reduced pressure
- extractionThe aqueous phase was extracted three times with 50 ml each time of ethyl acetate
- dry with materialThe combined organic extracts were dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b17fbaf1723c49f3abfbe6e380f86e20
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
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