Trimethylamine → (-)-Carnitine

HRID 2259460Notes

Reaction equation

HRID 2259460 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].CS(O)(=O)=O.[OH:10][C@@H:11]1[CH2:16][O:15][C:13](=[O:14])[CH2:12]1>O>[OH:10][C@H:11]([CH2:12][C:13](=[O:14])[O-:15])[CH2:16][N+:2]([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 1146Trimethylamine2×HCID 86749138HCID 86749138, compound

Product 1

HCID 10917(-)-Carnitine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an aqueous solution of trimethylamine (250 mL), 25% by weight solution of trimethylamine in water, is added (S)-3-hydroxybutyrolactone methane sulfonate (98 g, 0.5 mol) prepared as described above. The resulting solution is stirred at room temperature 1 hr, and then heated at 100° C. in a sealed vessel for 16 hrs. Upon cooling the solution to room temperature, the reaction mixture is evaporated to dryness in vacuo using ethanol and toluene (5:1) to remove residual water by azeotropic distillation. The crude L-carnitine is triturated with anhydrous acetone (100 ml) and the purified L-carnitine thus produced is collected by filtration. [α]D22 -31° (c 10.0, H2O).

Workup

  1. customprepared
  2. temperatureheated at 100° C. in a sealed vessel for 16 hrs
  3. temperatureUpon cooling the solution to room temperature
  4. customthe reaction mixture is evaporated to dryness in vacuo
  5. customto remove residual water
  6. distillationby azeotropic distillation
  7. customThe crude L-carnitine is triturated with anhydrous acetone (100 ml)

Sources & evidence

ORD record
ord-18f58fdfa26f408a99d4dd422486e7c9
Source dataset
uspto-grants-1995_12
Patent number
US05473104

Reaction notes

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