Réaction #2267064

Équation de réaction

6,7-Dimethoxy-1-methyl-3,4-dihydroxyisoquinoline

formic acid-triethylamine

sodium carbonate

→

(S)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

Rendement 99.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Extractionto extract the product in ethyl acetate
2. 2
   AutreAfter evaporation of the solvent, 1H-NMR(CDCl3) of the resulting product
3. 3
   AutreThen, the product was purified by silica gel chromatography

Mode opératoire

6,7-Dimethoxy-1-methyl-3,4-dihydroxyisoquinoline (Table 6-2a) (1.03 g, 5 mmol) and a ruthenium catalyst (Table 7) (R, R)-1a (16 mg, 0.025 mmol) were dissolved in acetonitrile (10 ml), followed by addition of a mixture of formic acid-triethylamine (5:2), for agitation at 28° C. for 3 hours. To the reaction mixture was added an aqueous sodium carbonate solution to extract the product in ethyl acetate. After evaporation of the solvent, 1H-NMR(CDCl3) of the resulting product was measured to calculate the conversion. Then, the product was purified by silica gel chromatography, to determine the optical purity and absolute configuration of the resulting optically active amine by HPLC or GLC. As collectively shown in Table 8, (S)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (1.02 g, yield of 99%, 96% ee) was obtained.

Source