R和S-1-(3′-溴-4′-甲氧基)苄基-2-甲基-6-甲氧基-7-羟基-1,2,3,4-四氢异喹啉的合成  

Synthesis of R and S-1-(3'-Bromo-4'-methoxy) benzyl-2-Methyl-6-Methoxy-7-hydroxy-1, 2, 3, 4-Tetrahydroisoquinoline

作　　者：邓定安[1] 蔡俊超[1] 

机构地区：[1]中国科学院上海药物研究所,上海200031

出　　处：《有机化学》1992年第1期87-91,共5页Chinese Journal of Organic Chemistry

摘　　要：单醚链和双醚链的节基四氢异喹啉在生物碱中较为长见。一般合成这类四氢异喹啉,是合成在一定位置上有溴的四氢异喹啉。R- and S-1-(3′-bromo-1′-methoxy)benzyl-2-methyl-6-methoxy-7-hydroxy-1,2, 3, 4-tetrahydroisoquinoline(8 and 9)are useful intermediates in the synthesis of tetre-hydroisoquinoline alkaloids. (RS)-1-(3′-bromo-4′-methoxy)benzyl-6-methoxy-7-benzyl-oxy-3, 4-dihydroisoquinoline (1) was reduced to (RS) -1-(3′-bromo-4′-methoxy) benzyl-6-methoxy-7′-benzyloxy-1,2,3, 4-tetrahydroisoquinoline (2) by sodium borohydride. Twochiral enantiomers (3) and (5) of 2 were resolved with di-p-tolouyl-D-(-)-tartaric acid.3 and 5 were converted to the N-methyl derivatives (6) and (7) with formaldehyde andformic acid respectively. Hydrolysis of 6 and 7 With hydrochloric acid gave 8 and 9. Abso-lute configuration of the compounds were assigned based on data of specific rotation and op-tical rotatory dispersion curves by using the convention and sequence rule (+)=S= (L);(-)=R=(D) in the benzyltetrahydroisoquinolin series.

关 键 词：手性 四氢异喹啉 拆分 合成 

分 类 号：O626.325[理学—有机化学]