(R)-1-<(tert-butoxycarbonyl)methyl>-6-methoxy-1,2,3,4-tetrahydroisoquinoline | 142946-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-1-<(tert-butoxycarbonyl)methyl>-6-methoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 142946-32-5
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: WDBFQNUIFSHDTA-CQSZACIVSA-N

反应信息

• 作为产物：
  描述：

  在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 1-(4-氨基-3-硝基苯基)-2-溴乙酮 、 (R)-1-<(tert-butoxycarbonyl)methyl>-6-methoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Chiral formamidines. The total asymmetric synthesis of (-)-8-azaestrone and related (-)-8-aza-12-oxo-17-desoxoestrone

  摘要：

  Attachment of the chiral formamidine moiety to 6-methoxy-1,2,3,4-tetrahydroisoquinoline afforded the key chiral, nonracemic precursor 8, upon which the azasteroid skeleton was constructed. Asymmetric alkylation with alpha-halo esters or beta-halo ethers gave 15 and 22, respectively, in high ee's. Cyclization, following enamine formation with cyclopentanedione or cyclopentanone, led to the chiral steroidal skeletons 6 and 5, respectively. The final stereocenters, leading to 8-azaestrone 4 with unnatural absolute configuration (antipodal), were accomplished by intramolecular alkylation of (+)-6b and subsequent reduction and ether cleavage. For the 12-oxosteroid 3, the methyl at C-13 was inserted by initial conjupte reduction of the enone 5 with a copper hydride reagent method) requiring the presence of a silyl chloride affording 21. The addition of methyl iodide to C-13 occurred after transforming the triethylsilyl enol ether, 21, to its lithium enolate. Stereochemical assignments for both azasteroids 3 and 4 were confirmed by spectroscopic means including circular dichroism curves.

  DOI：

  10.1021/jo00043a036