Pipecolic Acid → 1-(Ethoxycarbonyl)piperidine-2-carboxylic acid

HRID 2380215Notes

Reaction equation

HRID 2380215 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>O>[CH2:20]([O:19][C:17]([N:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4])=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 849Pipecolic AcidHCID 10928Ethyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 148109391-(Ethoxycarbonyl)piperidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.0 g (0.116 moles) of (±) pipecolic acid were dissolved in 180 ml of water. 25.5 g (0.185 moles) of potassium carbonate were added and the solution cooled to +5° C. 19.83 g (0.183 moles) of ethyl chloroformate were added dropwise under mechanical stirring, maintaining the temperature below +10° C. After 4 hours the reaction mixture was extracted with methylene chloride; the aqueous layer were treated with conc. HCl to acidic pH, extracted with methylene chloride (400 ml) which was dried over Na2SO4 and the solvent evaporated to dryness to afford 23.8 g of the crude product. Crystallization from isopropyl ether/n-hexane gave 21.7 g (93% of the theoretical) of the title compound.

Workup

  1. temperaturethe solution cooled to +5° C
  2. temperaturemaintaining the temperature below +10° C
  3. extractionAfter 4 hours the reaction mixture was extracted with methylene chloride
  4. additionthe aqueous layer were treated with conc. HCl to acidic pH
  5. extractionextracted with methylene chloride (400 ml) which
  6. dry with materialwas dried over Na2SO4
  7. customthe solvent evaporated to dryness
  8. customto afford 23.8 g of the crude product
  9. customCrystallization from isopropyl ether/n-hexane

Sources & evidence

ORD record
ord-7e60a3edc2d64d4491155ab2b0cf500b
Source dataset
uspto-grants-1994_11
Patent number
US05366981

Reaction notes

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