Réaction #2487411

Équation de réaction

DCC

R-lipoic acid

N,N-dimethylethanolamine

→

desired product

Rendement 79.0%

(R)-2-(dimethylamino)ethyl 5-(1,2-dithiolan-3-yl)pentanoate

Rendement 79.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONaddition
2. 2
   Autrethe cold bath was removed
3. 3
   Autreall volatiles were removed under reduced pressure
4. 4
   Autrethe resulting residue was purified by flash column chromatography (SiO2, 2% MeOH in CH2Cl2)

Mode opératoire

A solution of DCC (11 g, 53 mmol) in anhydrous CH2Cl2 (20 mL) was added with stirring over 10-20 minutes to a cold (0° C.) solution of R-lipoic acid (10.0 g, 48.5 mmol), N,N-dimethylethanolamine (14.5 mL, 145 mmol, 3 eq.), and DMAP (600 mg, 4.9 mmol) in anhydrous CH2Cl2 (50 mL). Following complete addition, the cold bath was removed. After 18 hours at room temperature, all volatiles were removed under reduced pressure, and the resulting residue was purified by flash column chromatography (SiO2, 2% MeOH in CH2Cl2) providing the desired product as a clear yellow oil (10.6 g, 79%). All data consistent with values reported in the literature. (See Courvoisier C. et al. 2006. Synthesis and effects of 3-methylthiopropanoyl thiolesters of lipoic acid, methional metabolite mimics. Bioorganic Chemistry 34(1):49-58.)

Source