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

HRID 914154Notes

Reaction equation

HRID 914154 reaction equation
C([N:8]([CH:18]1[CH2:23][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][CH2:23]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57955523HCID 57955523, compound

Product 1

HCID 57955635Ethyl 3-(cyclohexylamino)-2-fluoro-2-methylpropanoateYield 95.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(benzyl(cyclohexyl)amino)-2-fluoro-2-methylpropanoate (1.6 g, 5 mmol) in ethanol (20 mL) was hydrogenated with Pd(OH)2 (20%, 176 mg, 0.25 mmol) in presence of TFA (5 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 (1.1 g, 95%) as light yellow liquid. [M+H] calc'd for C12H22FNO2, 232. found 232.

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-f2961bc484774543b131415606d69edf
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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