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

HRID 914144Notes

Reaction equation

HRID 914144 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-c20db01a52c34d93aa445c92030a22ba
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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