HCID 86670987, compound → HCID 86670988, compound

HRID 515360Notes

Reaction equation

HRID 515360 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

5

Reactant 2

HCID 86670987HCID 86670987, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86670988HCID 86670988, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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]+

Workup

  1. customwas consumed
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. washChromatography on silica, eluting with ethyl acetate

Sources & evidence

ORD record
ord-d6118d43242d4d7baa4e21ca55471feb
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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