HCID 22261569, compound → HCID 22261478, compound

HRID 1610582Notes

Reaction equation

HRID 1610582 reaction equation
[NH2:1][CH:2]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:32])([F:31])[CH:28]([F:30])[F:29])[CH:21]=1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]CC2C=CC=CC=2)[CH:6]=1)[OH:4]>C(O)C.[Pd]>[NH2:1][CH:2]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:31])([F:32])[CH:28]([F:29])[F:30])[CH:21]=1)[CH:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[OH:4]

Participants

4

Reactant 1

HCID 22261569HCID 22261569, compound

Product 1

HCID 22261478HCID 22261478, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1RS,2SR)-2-amino-1-[3-(benzyloxy)-phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propan-1-ol (5.50 g, 12.23 mmol) in ethanol (100 ml) was added 10% palladium/carbon (containing water by 50%, 500 mg), and the mixture was stirred under a hydrogen stream overnight. The catalyst was removed from the reaction solution using celite, and the filtrate was concentrated to give the objective substance (4.04 g, 92%, crude). To obtain data, a portion was purified by alumina column chromatography (ethanol) and recrystallized from diisopropyl, ether-hexane.

Workup

  1. customThe catalyst was removed from the reaction solution
  2. concentrationthe filtrate was concentrated
  3. customto give the objective substance (4.04 g, 92%, crude)
  4. customTo obtain data
  5. customa portion was purified by alumina column chromatography (ethanol)
  6. customrecrystallized from diisopropyl, ether-hexane

Sources & evidence

ORD record
ord-81f2f9757bfd42cf885d70e16d792576
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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