Sodium Hydroxide → 4-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)butanoic acid

HRID 974961Notes

Reaction equation

HRID 974961 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10334920Tert-butyl 4-(4-ethoxy-4-oxobutyl)piperidine-1-carboxylate

Product 1

HCID 104009874-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)butanoic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution (2 ml) of 700 mg of NaOH was added to 15 ml of a methanol solution of 1.0 g of ethyl 4-(1-t-butyloxycarbonyl-4-piperidyl)butanoate and stirred for 1 hour at room temperature. The methanol was removed by distillation under a reduced pressure, and the residue was made acidic with 1N HCl and then extracted with ethyl acetate. This was washed with brine, dried with magnesium sulfate, and the solvent was removed by distillation under a reduced pressure. Thus, 0.91 g of 4-(1-t-butyloxycarbonyl-4-piperidyl)butanoic acid was obtained as a white solid.

Workup

  1. customThe methanol was removed by distillation under a reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThis was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was removed by distillation under a reduced pressure

Sources & evidence

ORD record
ord-63499806f1d8478385b2ec80ef2d05f4
Source dataset
uspto-grants-1997_03
Patent number
US05607948

Reaction notes

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