Pipecolic Acid → HCID 574442, compound

HRID 2272859Notes

Reaction equation

HRID 2272859 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].[C:10](OC(=O)C)(=[O:12])C.O>C(O)=O.CO>[CH:10]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8])=[O:12]

Participants

6

Reactant 3

HCID 849Pipecolic AcidHCID 962WaterHCID 7918Acetic Anhydride

Product 1

HCID 574442HCID 574442, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 40 g of a racemic mixture of 2-piperidinecarboxylic acid (0.310 mmol) in 300 mL of formic acid at 0° C. there are added dropwise 200 mL (2.15 mmol) of acetic anhydride. The whole is then stirred at ambient temperature overnight. The reaction mixture is then cooled to 0° C., hydrolysed by the addition of 250 mL of water and stirred for half an hour at 0° C. before being concentrated to dryness. The oil so obtained is taken up in 200 mL of methanol and then concentrated to dryness. The title product is obtained in the form of an oil with a yield of 98%. It is used directly, without further purification, for the following step.

Workup

  1. stirringstirred for half an hour at 0° C.
  2. concentrationbefore being concentrated to dryness
  3. customThe oil so obtained
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ed120d54d4bd400da890504aab0423c3
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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