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

HRID 418779Notes

Reaction equation

HRID 418779 reaction equation
[F:1][C:2]([F:29])([F:28])[C@@:3]([CH2:18][NH:19][C@@H](C1C=CC=CC=1)C)([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]>CCO.[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:29])([F:28])[F:1]

Participants

4

Reactant 1

HCID 66648435(2R)-1,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol2×

Product 1

HCID 59010010(2R)-2-(aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanolYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2R)-1,1,1-Trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol (Intermediate 20) (200 mg, 0.48 mmol) was dissolved in EtOH (8 mL) and hydrogenated over 10% palladium on charcoal (100 mg) at 53 psi and room temperature for 16 hours. Catalyst was removed by filtration through celite. The celite was washed several times with EtOH. The filtrate was evaporated in vacuo to give the title compound as a pale yellow oil (158 mg).

Workup

  1. customCatalyst was removed by filtration through celite
  2. washThe celite was washed several times with EtOH
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1365a1aa9f7f4450b3047bb1608da1c7
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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