Trifluoroacetic acid → 3-(3-Ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine
Reaction equation
[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([F:26])[CH:16]=3)[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[O:6][N:5]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:23])[F:24])=[C:17]([F:26])[CH:16]=3)[CH2:12][NH:11][CH2:10]2)[O:6][N:5]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
387 mg (0.50 mmol) of tert-butyl 3-(3-ethoxy-1,2,4-oxadiazol-5-yl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine-1-carboxylate were initially charged in 30 ml of dichloromethane and admixed with 0.38 ml (567 mg, 4.97 mmol) of trifluoroacetic acid. The reaction mixture was stirred at RT for 16 hours, admixed with the same amount of trifluoroacetic acid and stirred at RT for a further 3.5 hours. The reaction mixture was concentrated under reduced pressure, taken up in ethyl acetate and washed twice with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 195 mg (96% of theory)
Workup
- stirringstirred at RT for a further 3.5 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- washwashed twice with saturated aqueous sodium hydrogencarbonate solution
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8dfc9d2fbe7246ae96be280ae50fa4b3
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084469B2
Reaction notes
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