반응 #2267064

반응 방정식

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

formic acid-triethylamine

sodium carbonate

→

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

수율 99.0%

용매

acetonitrile

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후처리

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

실험 절차

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.

출처