Trifluoroacetic acid → Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoate

HRID 1880935Notes

Reaction equation

HRID 1880935 reaction equation
C([N:8]([CH2:14][C:15]([F:23])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(O)C.[OH-].[OH-].[Pd+2]>[CH:9]1([NH:8][CH2:14][C:15]([F:23])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57955532Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate

Product 1

HCID 57955590Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoateYield 88%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate (2.2 g, 6.8 mmol) in ethanol (20 mL) was hydrogenated with Pd(OH)2 (20%, 240 mg, 0.34 mmol) in presence of TFA (6.8 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 (1.38 g, 88%) as light yellow liquid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95 (t, J=7.6 Hz, 3 H) 1.31 (t, J=7.1 Hz, 4 H) 1.41-1.94 (m, 9 H) 2.88-3.08 (m, 3 H) 4.26 (qd, J=7.12, 2.40 Hz, 2 H). [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-e4f6e835d6b2431a8253c7b65b283e45
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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