Potassium Hydroxide → 3-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

HRID 2185564Notes

Reaction equation

HRID 2185564 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:22])[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)C>O.CCO>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([CH2:8][CH2:7][C:6]([OH:22])=[O:5])[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 23245138tert-Butyl 4-(3-ethoxy-3-oxopropyl)piperidine-1-carboxylate

Product 1

HCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of KOH (86%, 0.42 g, 6.4 mmol) in water (1.5 mL) was added to a solution of 3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionic acid ethyl ester in 95% EtOH (15 mL) at rt. After 2.5 h, the mixture was partitioned between EtOAc (50 mL) and 2 N aq. HCl (50 mL). After extraction of the aqueous layer with EtOAc (50 mL), the organic layers were washed with sat'd NaCl (25 mL), dried (Na2SO4), decanted, and evaporated to give 1.06 g of the title compound as a crystalline solid.

Workup

  1. customthe mixture was partitioned between EtOAc (50 mL) and 2 N aq. HCl (50 mL)
  2. extractionAfter extraction of the aqueous layer with EtOAc (50 mL)
  3. washthe organic layers were washed with sat'd NaCl (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. customevaporated

Sources & evidence

ORD record
ord-84ac710993d7447f9f634083b8ed4d4f
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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