Trimethylamine → (-)-Carnitine

HRID 1920280Notes

Reaction equation

HRID 1920280 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:6])[CH3:5].Cl[CH2:8][C@H:9]([OH:16])[CH2:10][C:11]([O:13]CC)=[O:12]>O>[OH:16][C@H:9]([CH2:10][C:11](=[O:12])[O-:13])[CH2:8][N+:4]([CH3:6])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 14798Sodium HydroxideHCID 27344454-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-

Product 1

HCID 10917(-)-Carnitine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydroxide (156.1 g, 3.9 mol, 1.4 eq) was dissolved in water (3700 g). Aqueous tri-methylamine (25%, 649.5 g, 1.0 eq) was added with cooling. The resulting mixture was cooled to 0° C. and ethyl (R)-4-chloro-3-hydroxybutyrate (content 91.5%, 500.0 g, 2.75 mol) was added dropwise within 3 h to the stirred reaction mixture. After one additional hour at 0° C. the reaction mixture was warmed to +20° C. and analyzed by HPLC.

Workup

  1. temperaturewith cooling
  2. temperatureAfter one additional hour at 0° C. the reaction mixture was warmed to +20° C.

Sources & evidence

ORD record
ord-7d0a8d78a9ff43dcabfd74deaf3b232d
Source dataset
uspto-grants-2012_05
Patent number
US08168823B2

Reaction notes

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