1,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-{[(phenylmethyl)amino]methyl}-2-pentanol → 2-(Aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanol

HRID 418777Notes

Reaction equation

HRID 418777 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]([CH2:18][NH:19]CC1C=CC=CC=1)([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[H][H]>C(O)C.[Pd]>[NH2:19][CH2:18][C:3]([OH:17])([CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6])[C:2]([F:28])([F:27])[F:1]

Participants

5

Reactant 2

HCID 576159391,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-{[(phenylmethyl)amino]methyl}-2-pentanol2×HCID 178418361HCID 178418361, compound

Product 1

HCID 179365862-(Aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanolYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-{[(phenylmethyl)amino]methyl}-2-pentanol (Intermediate 17, 63 g, 0.158 mol) was added to a stirred solution of 10% Pd/C (12.6 g, 50% wet) in ethanol (1.07 L) at 20° C. in a nitrogen purged vessel. The mixture was hydrogenated at 20° C. and atmospheric pressure until there was no further hydrogen uptake. The suspension was then filtered through Celite and glass fibre filter paper to remove the catalyst, and the cake washed with ethanol (120 mL). The combined filtrate and washings were evaporated under reduced pressure to give the title compound as a light grey solid (47.5 g).

Workup

  1. customwas hydrogenated at 20° C.
  2. filtrationThe suspension was then filtered through Celite and glass fibre filter paper
  3. customto remove the catalyst
  4. washthe cake washed with ethanol (120 mL)
  5. customThe combined filtrate and washings were evaporated under reduced pressure

Sources & evidence

ORD record
ord-c668de29d48740daa33fa42f76e54478
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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