Water → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 1643436Notes

Reaction equation

HRID 1643436 reaction equation
O.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.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:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]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

Water (75 ml) was added to piperidine-4-carboxylic acid (25 g) in THF (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 subsequently stirred at room temperature for 5 h (TLC control). When the reaction was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml), and the mixture was washed with ethyl acetate (2×150 ml). The aqueous phase was rendered acidic with dilute aqueous HCl and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96%)

Workup

  1. distillationthe organic solvent was distilled off
  2. washthe mixture was washed 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-36c9ad1b19354cc58114b52a0d7c4812
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

Loading…