Trifluoroacetic acid → methyl {(2S,3R)-2-[4-(trifluoromethyl)phenyl]piperidin-3-yl}acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[C@@H:6]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:24]([F:25])([F:27])[C:21]1[CH:20]=[CH:19][C:18]([C@@H:6]2[C@@H:5]([CH2:4][C:3]([O:2][CH3:1])=[O:28])[CH2:10][CH2:9][CH2:8][NH:7]2)=[CH:23][CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the resulting tert-butyl (2S,3R)-3-(2-methoxy-2-oxoethyl)-2-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate (2.8 g, 7.0 mmol) in DCM (50 mL) was treated with TFA (2.7 mL, 35 mmol) and stirred at ambient temperature for 16 hours. The reaction mixture was evaporated in vacuo and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated in vacuo to give methyl {(2S,3R)-2-[4-(trifluoromethyl)phenyl]piperidin-3-yl}acetate. LC/MS (EIMS, M+H)=302.1.