HCID 86670987, compound → HCID 86670988, compound

Reaction equation

[F:1][C:2]([F:33])([F:32])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H][H]>[Pd].C(OCC)(=O)C>[NH2:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[O:22][CH:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:33])([F:1])[F:32])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=2)[CH2:17][CH2:18]1

Participants

Procedure

A mixture of 1,1,1,3,3,3-hexafluoro-2-(4-((4-(3-nitrophenoxy)piperidin-1-yl)methyl)-phenyl)propan-2-ol (8.36 mmol, 4 g) and palladium on carbon (10%) (0.251 mmol, 0.267 g) in ethyl acetate was hydrogenated at 3 bar until the desired amount of hydrogen was consumed. The reaction was filtered through celite and concentrated under reduced pressure. Chromatography on silica, eluting with ethyl acetate, gave the title compound (3.7 g). MS (ESI) m/z 449.2 [M+H]+