Pipecolic Acid → HCID 574442, compound

HRID 518911Notes

Reaction equation

HRID 518911 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-piperidine-carboxylic acid (0.310 mmol) in 300 mL of formic acid placed at 0° C. there are added, dropwise, 200 mL (2.15 mmol) of acetic anhydride. The batch is then stirred at ambient temperature overnight. Then, the reaction mixture is cooled to 0° C., hydrolysed by adding 250 mL of water, and stirred for half an hour at 0° C. before being concentrated to dryness. The oil thereby 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 in a yield of 98%. It is used directly, without being otherwise purified, in the next Step.

Workup

  1. customplaced at 0° C.
  2. additionthere are added
  3. temperatureThen, the reaction mixture is cooled to 0° C.
  4. stirringstirred for half an hour at 0° C.
  5. concentrationbefore being concentrated to dryness
  6. customThe oil thereby obtained
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f03a59b6d0234d7d870d0b3a48029bf0
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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