Trifluoroacetic acid → HCID 66670206, compound

HRID 1514641Notes

Reaction equation

HRID 1514641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)=[CH:13][C:12]([C:22]([O:24]C(C)(C)C)=[O:23])=[C:11]2[CH3:29])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14]([CH:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)=[CH:13][C:12]([C:22]([OH:24])=[O:23])=[C:11]2[CH3:29])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66670175tert-butyl 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxylate

Product 1

HCID 66670206HCID 66670206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 230 mg portion of tert-butyl 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxylate was dissolved in 2 ml of dichloromethane, and 1 ml of trifluoroacetic acid was added under ice-cooling, followed by stirring at room temperature for 1.5 hours. The reaction liquid was concentrated under a reduced pressure, and a saturated sodium bicarbonate aqueous solution was added, followed by three times extractions with chloroform. After drying the organic layer with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (methanol:chloroform=10:90-15:85-20:80) to obtain 124 mg of 1-[2-(4-fluorophenyl)ethyl]-2-methyl-5-(1-methylpiperidin-4-yl)-1H-pyrrole-3-carboxylic acid as a colorless solid.

Workup

  1. temperaturecooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under a reduced pressure
  4. additiona saturated sodium bicarbonate aqueous solution was added
  5. extractionfollowed by three times extractions with chloroform
  6. dry with materialAfter drying the organic layer with anhydrous sodium sulfate
  7. customthe solvent was evaporated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methanol:chloroform=10:90-15:85-20:80)

Sources & evidence

ORD record
ord-833df55f92f84f6fb33a84144abec1df
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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