(1RS,2SR)-2-amino-1-[4-(benzyloxy)phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propan-1-ol → 4-{(1RS,2SR)-2-amino-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenol

HRID 1610570Notes

Reaction equation

HRID 1610570 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][C:8]([O:11]CC2C=CC=CC=2)=[CH:7][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:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[OH:4]

Participants

4

Reactant 1

HCID 22261439(1RS,2SR)-2-amino-1-[4-(benzyloxy)phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propan-1-ol

Product 1

HCID 222620024-{(1RS,2SR)-2-amino-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (1RS,2SR)-2-amino-1-[4-(benzyloxy)phenyl]-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-propan-1-ol (2.60 g, 5.79 mmol) in ethanol (20 ml) was added 10% palladium/carbon (containing water by 50%, 260 mg), and the mixture was stirred overnight under a hydrogen stream. The catalyst was removed from the reaction solution using celite, and the filtrate was concentrated. The residue was purified neutral alumina column chromatography (ethanol) to give the objective substance (0.80 g, 39%) as an amorphous compound.

Workup

  1. customThe catalyst was removed from the reaction solution
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified neutral alumina column chromatography (ethanol)
  4. customto give the objective substance (0.80 g, 39%) as an amorphous compound

Sources & evidence

ORD record
ord-d74d5e71d21b4917a081e4e350729c63
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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