Pipecolic Acid → HCID 49759835, compound

HRID 1166430Notes

Reaction equation

HRID 1166430 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].[C:10]([OH:19])(=[O:18])[CH:11]([CH:13]([C:15]([OH:17])=[O:16])[OH:14])[OH:12]>C(O)C.O>[C:15]([CH:13]([CH:11]([C:10]([OH:19])=[O:18])[OH:12])[OH:14])([OH:17])=[O:16].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 849Pipecolic AcidHCID 8752,3-Dihydroxybutanedioic Acid

Product 1

HCID 49759835HCID 49759835, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Piperidinecarboxylic acid (26 g, 0.201 mol) and (+)-tartaric acid (31.2 g, 0.208 mol) were suspended in a mixture of ethanol (400 ml) and water (25 ml). The mixture was heated to 80° C., and the solution was allowed to cool to room temperature. The precipitated solid was filtered off, washed with ethanol and dried to give 25.4 g (45%) (R)-(+)-2-piperidinecarboxylic acid (+)-tartrate. The mother liquor was evaporated in vacuo, and the residue was dissolved in water (120 ml). A solution of potassium hydroxide (6.5 g, 116 mmol) in water (13 ml) was added, and the precipitated mono potassium tartrate was removed by filtration. Evaporation of the filtrate in vacuo afforded 19.5 g crude (S)-(−)-2-piperidinecarboxylic acid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-b707036d950c4df5926a9fa6b4b71663
Source dataset
uspto-grants-2003_09
Patent number
US06613791B1

Reaction notes

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