Trimethylamine → (-)-Carnitine

HRID 1920281Notes

Reaction equation

HRID 1920281 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].[OH-].[Na+]>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

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

In a 250 mL reactor, ethyl (R)-4-chloro-3-hydroxybutyrate (content 94%, 12.00 g, 67.7 mmol) was stirred with water (75.04 g) and cooled to 0° C. Aqueous trimethylamine (25%, 17.71 g, 1.1 eq.) was added at once at 0° C., followed by dropwise addition of aqueous sodium hydroxide (25%, 15.30 g, 1.4 eq.) within 3 h. After another 1 h at 0° C. the reaction mixture was allowed to warm to 20° C. and analyzed by HPLC.

Workup

  1. temperatureto warm to 20° C.

Sources & evidence

ORD record
ord-c7c9a2cc172d43d1864f1bec9486c0b7
Source dataset
uspto-grants-2012_05
Patent number
US08168823B2

Reaction notes

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