Lithium Hydroxide → 1-[(Tert-butoxy)carbonyl]-4-ethylpiperidine-4-carboxylic acid

HRID 566410Notes

Reaction equation

HRID 566410 reaction equation
C([O:3][C:4](=[O:20])[C:5]1([CH2:18][CH3:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)C.[OH-].[Li+]>C(O)C>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH2:18][CH3:19])([C:4]([OH:20])=[O:3])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 53393415Ethyl 1-Boc-4-ethyl-4-piperidine carboxylate

Product 1

HCID 221690971-[(Tert-butoxy)carbonyl]-4-ethylpiperidine-4-carboxylic acidYield 45.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-4-ethylisonipecotic acid ethyl ester (570 mg) in ethanol (10 ml) was added a 1M lithium hydroxide solution (8 ml), and the mixture was refluxed under heating for 20 hours. Then, the reaction mixture was concentrated, and water was added to the residue. The aqueous layer was washed with ether, acidified with 1N hydrochloric acid, and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (233 mg, yield 45%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 20 hours
  3. concentrationThen, the reaction mixture was concentrated
  4. additionwater was added to the residue
  5. washThe aqueous layer was washed with ether
  6. extractionextracted with ether
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12634d9262c8429abd611d9741319fa7
Source dataset
uspto-grants-2001_01
Patent number
US06174887B1

Reaction notes

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