文章摘要
刘斌,朱周静.RSL3中间体的简便合成[J].精细化工,2019,36(5):
RSL3中间体的简便合成
A Convenient Synthesis of RSL3 Intermediate
投稿时间:2018-08-25  修订日期:2018-12-10
DOI:
中文关键词: RSL3  中间体  Pictet-Spengler反应  四氢-β-咔啉  构型
英文关键词: RSL3  intermediate  Pictet-Spengler reaction  tetrahydro-β-carboline  configuration
基金项目:陕西省自然科学基础研究计划(面上)项目(2018JM7046), 陕西省教育厅2018年度专项科学研究计划项目(18JK0954), 陕西省大学生创新创业项目(201849013)
作者单位E-mail
刘斌 陕西国际商贸学院 lb125lb@163.com 
朱周静 陕西国际商贸学院  
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中文摘要:
      以D-色氨酸为原料,通过酯化、Pictet-Spengler两步反应,简便有效地合成了RSL3的关键中间体(1S,3R)-1-[4-(甲氧羰基)苯基]-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸甲酯盐酸盐。对Pictet-Spengler反应条件进行了考察。结果表明:当n(D-色氨酸甲酯盐酸盐):n(4-甲酰基苯甲酸甲酯)=1:1.1、乙腈为反应溶剂,回流反应6 h,通过减压抽滤即可得到trans-构型产物(RSL3中间体)。产物及中间体经过1HNMR,1H-1H NOESY和ESI-MS进行确认。
英文摘要:
      (1S, 3R)-methyl 1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3- carboxylate hydrochloride, the key intermediate of RSL3, was synthesized by an efficient and parctical method from D-Tryptophan through a two-step reaction, involving esterification and Pictet-Spengler reaction. The Pictet-Spengler reaction conditions were investigated, and the optimal conditions were as follows: the molar ratio of D-tryptophan methyl ester hydrochloride and methyl 4-formylbenzoate is 1:1.1, the mixture was stirred in acetonitrile and refluxing for 6 h. The trans-isomer (RSL3 intermediate) was obtained by suction filtration. The structures of intermediate and the product were confirmed by 1HNMR, 1H-1H NOESY and ESI-MS.
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