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

HRID 2059894Notes

Reaction equation

HRID 2059894 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].CO.[OH-].[Li+]>O>[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 3

HCID 887MethanolHCID 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 1

HCID 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 (0.3 g, 12.9 mmol) was added. The mixture was stirred for 3 d at room temperature, then methanol was distilled off under vacuum and ethyl acetate (50 ml) and HCl solution (1 mol/l, 10 ml) added to the residue. Phase separation, extraction with ethyl acetate (2×50 ml), the combined organic phases were dried over sodium sulfate and concentrated to small volume under vacuum. Yield: 1.56 g (98%)

Workup

  1. distillationmethanol was distilled off under vacuum and ethyl acetate (50 ml) and HCl solution (1 mol/l, 10 ml)
  2. additionadded to the residue
  3. customPhase separation, extraction with ethyl acetate (2×50 ml)
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-0bf454f0d1ae47f4afa316528a2c43c0
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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