Lithium Hydroxide → 4-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid

HRID 2388659Notes

Reaction equation

HRID 2388659 reaction equation
C[O:2][C:3](=[O:27])[CH:4](C)[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=1[CH3:25])(=[O:15])=[O:14].[OH-].[Li+]>O.CO>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH3:25])[C:16]([S:13]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])(=[O:14])=[O:15])=[C:21]([CH3:22])[CH:20]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67316484Methyl 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid Methyl Ester

Product 1

HCID 574771724-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic acid methyl ester (1.65 g, 4.3 mmol) was dissolved in water (10 ml) and methanol (35 ml), and lithium hydroxide was added (0.3 g, 12.9 mmol). The mixture was stirred at room temperature for 3 days, the methanol was then distilled off in vacuo and ethyl acetate (50 ml) and HCl solution (1 mol/l, 10 ml) were added to the residue. The phases were then separated, extraction was carried out with ethyl acetate (2×50 ml) and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The yield was 1.56 g (98%).

Workup

  1. distillationthe methanol was then distilled off in vacuo and ethyl acetate (50 ml) and HCl solution (1 mol/l, 10 ml)
  2. additionwere added to the residue
  3. customThe phases were then separated
  4. extractionextraction
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dfa832285b0484a9a2832a5db9dea7d
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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