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有机化学
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有机化学 ›› 1992, Vol. 12 ›› Issue (1): 87-91. 上一篇    下一篇

研究论文

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

邓定安;蔡俊超   

  1. 中国科学院上海药物研究所
  • 发布日期:1992-02-25

Synthesis of R and S-1-(3'-bromo-4'-methoxy) benzyl-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline

DENG DINGAN;CAI JUNCHAO   

  • Published:1992-02-25

本文报道了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。

关键词: 质子磁共振谱法, 消旋体拆分, 喹啉 P, 立体异构

The title compounds I are useful intermediates in the synthesis of tetrahydroisoquinoline alkaloids. (RS)-1-(3-Bromo-4-methoxy)benzyl-6-methoxy-7-benzyloxy-3,4-dihydroi soquinoline was reduced to (RS)-1-(3-bromo-4-methoxy)benzyl-6-methoxy-7-benzyloxy-1,2,3,4-tetr ahydroisoquinoline (II) by NaBH4. II was resolved with di-p-toluoyl-D-(-)-tartaric acid and the enantiomers were converted to the N-Me derivatives with CH2O and HCO2H resp., followed by hydrolysis with HCl to give I. Abs. configurations of I were assigned based on sp. rotation and ORD curves by using the convention and sequence rule (+) = S = (L); (-) = R = (D) in the benzyltetrahydroisoquinoline series.

Key words: MESOTOMY, PROTON MAGNETIC RESONANCE SPECTROMETRY, QUINOLINE P, STEREOISOMERISM

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