Trifluoroacetic acid → HCID 21990122, compound

HRID 1091294Notes

Reaction equation

HRID 1091294 reaction equation
C([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:19]([OH:25])([C:21]([F:24])([F:23])[F:22])=[O:20]>CO.[OH-].[Pd+2].[OH-]>[F:22][C:21]([F:24])([F:23])[C:19]([OH:25])=[O:20].[OH:18][CH:16]1[CH2:17][NH:14][CH2:15]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 21990122HCID 21990122, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1-Benzhydryl-3-hydroxyazetidine (3.0 g, 12.6 mmol) was dissolved in methanol (60 mL), and 10 mL of TFA and 10% palladium hydroxide (1.0 g) were added thereto. The mixture was stirred for 24 hours under a hydrogen stream at normal pressure. The catalyst was removed by filtration, water (100 mL) was added to the filtrate, and the mixture was washed three times with ether. The aqueous layer was concentrated under reduced pressure, and the title compound (2.33 g, 99%) was obtained as an amorphous matter.

Workup

  1. customThe catalyst was removed by filtration, water (100 mL)
  2. additionwas added to the filtrate
  3. washthe mixture was washed three times with ether
  4. concentrationThe aqueous layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a736cebb3d94cfc9ed81b37c1b4d49a
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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