Lithium hydroxide, monohydrate → HCID 42641652, compound

HRID 2382196Notes

Reaction equation

HRID 2382196 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][N:11]([CH2:14][C:15]([O:17]CC)=[O:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[Li].O>C1COCC1.CO>[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68735614HCID 68735614, compound

Product 1

HCID 42641652HCID 42641652, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetate (0.2 g, 0.49 mmol) in THF/MeOH (10 mL, 1:1) 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 3 with diluted HCl, extracted with DCM, and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to afford pure 2-(4-(phenyl(4-(trifluoromethyl)phenyl)methyl)piperidin-1-yl)acetic acid (0.07 g, 36% yield) as a 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 DCM
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-48b1d6168f804b99b2da475d9cce5470
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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