Water → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 2387929Notes

Reaction equation

HRID 2387929 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.O.C(=O)(O)[O-].[Na+].[C:16](Cl)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1>[CH2:19]([O:18][C:16]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To piperidine-4-carboxylic acid (25 g) in THF (75 ml) there was added water (75 ml) followed by sodium bicarbonate (30.8 g). The mixture was cooled to 0° C., and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred for 5 hours at room temperature (TLC monitoring). When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml) and washed with ethyl acetate (2×150 ml). The aqueous phase was acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo.

Workup

  1. distillationthe organic solvent was distilled off
  2. washwashed with ethyl acetate (2×150 ml)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec0252ce21af40f88a85ffedbd58d16d
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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