4-Piperidinecarboxylic acid → 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

HRID 1670005Notes

Reaction equation

HRID 1670005 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>O>[C:13]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12]

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of piperidine-4-carboxylic acid (1.29 g, 10.0 mmol) in water was added NaOH (800 mg, 20.0 mmol). When the reaction solution was clear, (BOC)2O (2.5 g, 11.0 mmol) was added, and the reaction mixture was stirred at rt for 12 h. The solvent was removed in vacuo, and the residue was diluted with 1N HCl and EtOAc. The organic layer was extracted with EtOAc, and the organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The product was used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with 1N HCl and EtOAc
  3. extractionThe organic layer was extracted with EtOAc
  4. dry with materialthe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-22294ed62e4649d69f1715dbb350bd98
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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