Sodium Hydroxide → (3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

HRID 365452Notes

Reaction equation

HRID 365452 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([O:16]CC)=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1514445Ethyl (S)-N-Boc-piperidine-3-carboxylate

Product 1

HCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(t-butoxycarbonyl)piperidine-3(S)-carboxylate (35.9 g, 0.099 mol) was dissolved in abs EtOH (70 mL), treated with 0.5N NaOH (418 mL, 0.209 mol), and heated at reflux for 0.75 h. The reaction mixture was cooled and extracted with EtOAc. The aqueous basic layer was cooled with ice, carefully acidified (pH 3) with 3N HCl and extracted with CH2Cl2 (3×100 mL). The organics were combined, dried (MgSO4), filtered, and concentrated to give the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.75 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with EtOAc
  5. temperatureThe aqueous basic layer was cooled with ice
  6. extractionextracted with CH2Cl2 (3×100 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8fbcab3ca18e44ce81692dc47618b2aa
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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