DL-Carnitine → (-)-Carnitine

Participants

Reaction Steps

In 700 ml of methanol are dissolved under heat 35.0 g (0.177 mole) of DL-carnitine hydrochloride, and the solution is passed through OH type strongly basic resin (DOWEX-1X8). The methanol solution is concentrated to obtain 28.3 g (0.175 mole) of DL-carnitine. To DL-carnitine are added 62.6 g (0.175 mole) of dibenzoyl-L(+)tartaric acid and 93 ml of methanol, and the mixture is dissolved under heat to form dibenzoyl-L( +)tartarates of D-carnitine and L-carnitine. The tartarates are cooled at a temperature of below -10° C. with stirring to fractionally crystallize L-carnitine dibenzoyl-L(+)tartarate. The tartarare is filtered and washed to give L-carnitine dibenzoyl-L(+)tartarate (yield 30.5 g, purity 93.0%). Recrystallization of the tartarate from 100 ml of methanol gives 23.9 g of L-carnitine dibenzoyl-L(+)tartarate as white crystal. [α]D25 =-96.0° (c=1, MeOH), m.p. 154° C. (dec.), purity 99.5%.

Provenance & Evidence