Ethanol → 1-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrole-3-carboxylic acid

HRID 925627Notes

Reaction equation

HRID 925627 reaction equation
C(O)C.[CH:4]1([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:25]=[CH:24][C:23]([C:26]([O:28]C)=[O:27])=[CH:22]4)=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5]1.[OH-].[Na+]>O>[CH:4]1([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22]4)=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)[CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 71599013HCID 71599013, compound

Product 1

HCID 715990141-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To an ethanol (8 mL) solution of methyl 1-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-1H-pyrrole-3-carboxylate (1.4 g) synthesized in Example 1, 6 N aqueous sodium hydroxide solution (1.32 mL) was added and the mixture was stirred at 60° C. for 4 hours. The reaction mixture was left to cool to room temperature and, after adding water, extracted with chloroform. The aqueous layer was neutralized with hydrochloric acid and extracted with chloroform. The combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give the titled compound as a colorless amorphous substance (1.22 g).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool to room temperature
  3. extractionextracted with chloroform
  4. extractionextracted with chloroform
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00350adf2bc04ebd91694a6fda2ff92f
Source dataset
uspto-grants-2016_03
Patent number
US09284324B2

Reaction notes

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