Water → 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid

HRID 1880212Notes

Reaction equation

HRID 1880212 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2([CH3:17])[CH2:16][CH2:15]2)=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-].C1COCC1.O>C(O)C>[CH3:17][C:14]1([C:12]([N:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[O:13])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 594381441-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 594381681-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid ethyl ester (6.34 g, 26.5 mmol) and LiOH (1.67 g, 39.7 mmol) were stirred in a mixture of ethanol (30 mL), THF (30 mL) and water (15 mL) for 90 min at ambient temperature. After evaporation of the volatiles the residue was taken up in dichloro methane and extracted with 1N HCl. The organic phase was dried over sodium sulfate, filtered and evaporated to yield the title product (4.8 g, 86%) as colorless solid.

Workup

  1. customAfter evaporation of the volatiles the residue
  2. extractionextracted with 1N HCl
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5d1bbb6d3d4b4532b28edfa91a752fb8
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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