Trifluoroacetic acid → Ethyl 3-(cyclopentylamino)-2-fluoro-2-methylpropanoate

HRID 1880915Notes

Reaction equation

HRID 1880915 reaction equation
C([N:8]([CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:9][C:10]([F:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(O)C.[OH-].[OH-].[Pd+2]>[CH:18]1([NH:8][CH2:9][C:10]([F:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57955642Ethyl 3-(benzyl(cyclopentyl)amino)-2-fluoro-2-methylpropanoate

Product 1

HCID 57955537Ethyl 3-(cyclopentylamino)-2-fluoro-2-methylpropanoateYield 85%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(benzyl(cyclopentyl)amino)-2-fluoro-2-methylpropanoate (3.5 g, 11.4 mmol) in ethanol (30 mL) was hydrogenated with Pd(OH)2 (20%, 400 mg, 0.57 mmol) in presence of TFA (11.4 mmol) at atmospheric pressure for 20 h. The reaction mixture was filtered through celite. The filtrate was concentrated and diluted to EtOAc/H2O, aqueous layer was basified to pH=11-12 by 1N NaOH. The organic layer was then dried and concentrated to give the product (2.1 g, 85%) as light yellow liquid. [M+H] calc'd for C11H20FNO2, 218; found 218.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted to EtOAc/H2O, aqueous layer
  4. customThe organic layer was then dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b747a7b2a1144018d4f566e68b0f66e
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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