Trifluoroacetic acid → 4-{[5-Cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}piperidine
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[C:17]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[N:18][O:19][C:20]=2[CH:21]2[CH2:23][CH2:22]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:21]1([C:20]2[O:19][N:18]=[C:17]([C:24]3[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=3[Cl:30])[C:16]=2[CH2:15][O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:22][CH2:23]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a cooled (ice bath) 500 mL flask under nitrogen, is added a solution of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (16 g, 34.3 mmol) in dichloromethane (80 mL). This is followed by dropwise addition of trifluoroacetic acid (80 mL) (added over 30 minutes). The reaction is stirred at room temperature for 90 min. The solvent is removed under vacuum, EtOAc is added (400 mL), and the mixture is washed with 2 N NaOH (2×250 mL) and brine. The organic layer is dried over MgSO4, filtered and evaporated to obtain the title compound as a brown oil (11.78 g, 93%). MS (m/e): 367 (M+1)