Lithium hydroxide, monohydrate → 2-(3-(Phenyl(4-(trifluoromethyl)-phenyl)methyl)piperidin-1-yl)acetic acid

HRID 2382189Notes

Reaction equation

HRID 2382189 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([O:17]CC)=[O:16])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[Li].O>C1COCC1.CO.O>[C:1]1([CH:7]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=2)[CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([OH:17])=[O:16])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68733022Ethyl 2-(3-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetate

Product 1

HCID 426416482-(3-(Phenyl(4-(trifluoromethyl)-phenyl)methyl)piperidin-1-yl)acetic acidYield 65%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 2-(3-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetate (0.5 g, 1.23 mmol) in THF/MeOH/water (12 mL, 7:3:2) at 5° C. was added LiOH.H2O (0.15 g, 3.7 mmol). After stirring at rt for 4 h, the solvent was removed under vacuum. The residue was diluted with water and the pH was adjusted to 4 with diluted HCl, extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was dissolved in ethyl acetate and crashed out of pentane at cool condition to afford pure 2-(3-(phenyl(4-(trifluoromethyl)-phenyl)methyl)piperidin-1-yl)acetic acid (0.3 g, 65% yield) as an off white solid. MS (ESI, pos. ion) m/z: 378 (M+1).

Workup

  1. customthe solvent was removed under vacuum
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. temperatureat cool condition

Sources & evidence

ORD record
ord-2c626dfc114242aa90c9a3e386e229f9
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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