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

HRID 1880925Notes

Reaction equation

HRID 1880925 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-c438cfcdfeb644b1801990040e84df75
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

Loading…