4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 482564Notes

Reaction equation

HRID 482564 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH:12]1[CH2:20][CH2:19][CH:15]([C:16]([OH:18])=[O:17])[CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O>[C:2]([N:12]1[CH2:20][CH2:19][CH:15]([C:16]([OH:18])=[O:17])[CH2:14][CH2:13]1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

6

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Benzyl chloroformate (16.4 mL, 115 mmol) in toluene (50 mL) was added dropwise to a stirred solution of 12.9 g (100 mmol) of isonipecotic acid (Aldrich) and 21.0 g (250 mmol) of sodium bicarbonate in 200 mL of water. After 14 h, the mixture was extracted with ether (3×50 ml) and the ether layers were discarded. The aqueous layer was acidified with conc. HCl to pH 2, causing the product to precipitate. The product was partitioned into ethyl acetate (3×50 mL) and the combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to yield 22.6 g (86%) of N-CBZ-isonipecotic acid as a viscous oil.

Workup

  1. extractionthe mixture was extracted with ether (3×50 ml)
  2. customto precipitate
  3. customThe product was partitioned into ethyl acetate (3×50 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87deec82e6494384a8b06ceec6ff8d7e
Source dataset
uspto-grants-1998_08
Patent number
US05798337

Reaction notes

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