Trifluoroacetic acid → 2-[4-(Methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine
Reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C(Cl)Cl>[CH3:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:22][N:23]=2)=[CH:14][CH:13]=1)(=[O:10])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
TFA (2 mL) was added to a solution of 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (705 mg, 1.58 mmol) in CH2Cl2 (50 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 give 460 mg (84%) of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (d, 1H, J=2.9 Hz), 8.29 (d, 2H, J=8.6 Hz), 8.08 (d, 1H, J=8.8 Hz), 8.00 (d, 2H, J=8.6 Hz), 7.55 (dd, 1H, Ja=8.8 Hz, Jb=3.0 Hz), 4.04 (d, 2H, J=6.2 Hz), 3.40-3.25 (m, 2H), 3.25 (s, 3H), 3.01-2.83 (m, 2H), 2.22-2.02 (m, 1H), 2.00-1.90 (m, 2H), 1.60-1.37 (m, 2H); LRMS (ESI), m/z 347 (M+H).