Trimethylamine → (-)-Carnitine

HRID 413513Notes

Reaction equation

HRID 413513 reaction equation
Cl[CH2:2][C@H:3]([OH:10])[CH2:4][C:5]([O:7]CC)=[O:6].[CH3:11][N:12]([CH3:14])[CH3:13]>O>[OH:10][C@H:3]([CH2:4][C:5](=[O:6])[O-:7])[CH2:2][N+:12]([CH3:14])([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 27344454-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-

Product 1

HCID 10917(-)-CarnitineYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

400 g of crude ethyl (+) (R)-4-chloro-3-hydroxybutyrate, prepared according to Example 8, and 1 l of 45% trimethylamine in H2O are placed in a 2-liter reactor. The reaction mixture is heated to 80° C. and kept at this temperature for 15 h. After cooling and removing the excess of trimethylamine under nitrogen flow, the aqueous solution is extracted with 1.9 l of methylene chloride and analyzed with HPLC. L-carnitine is obtained with 75% yield.

Workup

  1. customare placed in a 2-liter reactor
  2. temperatureAfter cooling
  3. customremoving the excess of trimethylamine under nitrogen flow
  4. extractionthe aqueous solution is extracted with 1.9 l of methylene chloride

Sources & evidence

ORD record
ord-c8f4026d15844e13a4a08c4f23aeab51
Source dataset
uspto-grants-2003_05
Patent number
US06566552B2

Reaction notes

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