HCID 23030621, compound → HCID 57986727, compound

HRID 1869578Notes

Reaction equation

HRID 1869578 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]([NH2:20])=O)[CH2:14][CH2:13]2)=[C:8]([F:21])[CH:7]=1)=[O:5])[CH3:2]>C1COCC1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]#[N:20])[CH2:16][CH2:17]2)=[C:8]([F:21])[CH:7]=1)[CH3:2]

Participants

5

Reactant 1

HCID 23030621HCID 23030621, compound

Product 1

HCID 57986727HCID 57986727, compoundYield 101.5%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 9845Trifluoroacetic anhydrideSolvent

Procedure

To a solution of 1.50 g of 1-(4-ethoxycarbonyl-2-fluorophenyl)piperidine-4-carboxamide in 20 ml of THF, 2.0 ml of triethylamine and 0.9 ml of trifluoroacetic acid anhydride were added at −78° C., and the mixture was stirred at room temperature for 6 hours. The solvent was evaporated, EtOAc was added, and then the organic layer was washed with water and brine, and dried over sodium sulfate. After the evaporation of the solvent, the residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=5:1˜4:1) to obtain 1.43 g of 4-(4-cyanopiperidino)-3-fluorobenzoic acid ethyl ester.

Workup

  1. customThe solvent was evaporated
  2. additionEtOAc was added
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customAfter the evaporation of the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=5:1˜4:1)

Sources & evidence

ORD record
ord-30a2a7d74c43467497174dccafac783f
Source dataset
uspto-grants-2009_12
Patent number
US07638536B2

Reaction notes

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