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

HRID 906042Notes

Reaction equation

HRID 906042 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O.O1CCOCC1>[CH2:20]([O:19][C:17]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 91%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of piperidine-4-carboxylic acid in a 1:1 mixture of H2O/dioxane (0.4 M), 5 eq of K2CO3 were added before dropwise introduction at 0° C. of 1.1 eq of benzyl chloroformate. The reaction was stirred at RT overnight. The reaction was first washed with Et2O. The aqueous phase was acidified to pH 2 with aqueous HCl (6N) before being extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give the product (91%); MS (ES+) m/z 264 (M+H)+

Workup

  1. washThe reaction was first washed with Et2O
  2. extractionbefore being extracted with EtOAc (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be4b3c7d37b94944a7c216c2e41f40f9
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

Loading…