Trifluoroacetic acid → HCID 58920017, compound

HRID 1365534Notes

Reaction equation

HRID 1365534 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][C:10]([F:24])([F:23])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C1C=CC=CC=1.C(O)(C(F)(F)F)=O>CCO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][C:10]([F:23])([F:24])[CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58920483HCID 58920483, compound

Product 1

HCID 58920017HCID 58920017, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 4-(3-(dibenzylamino)-2,2-difluoropropoxy)butanoate (120 mg, 0.29 mmol) in EtOH (1 mL) was added 50 mg Pd(OH)2 (10 mg, 20% on C) followed by the addition of TFA (25 μL). The reaction mixture was stirred at room temperature under H2 for 18 h. The solid was removed by filtration and the filtrate was concentrated under reduced pressure to yield tert-butyl 4-(3-amino-2,2-difluoropropoxy)butanoate (50 mg, 72% yield).

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-853c800da9fc4249a4acaea48066c61b
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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