(3R,4R)-tert-butyl 3-((6-(allyl(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate | 1221064-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,4R)-tert-butyl 3-((6-(allyl(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3R,4R)-3-hydroxy-4-[[4-methyl-6-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pyridin-2-yl]methyl]pyrrolidine-1-carboxylate
• CAS: 1221064-98-7
• 化学式: C₂₄H₃₇N₃O₅
• 分子量: 447.575
• InChiKey: JMJSDPAVAFLKBE-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl (3R,4R)-3-[[4-methyl-6-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]pyridin-2-yl]methyl]-4-[(2-methylpropan-2-yl)oxycarbonyloxy]pyrrolidine-1-carboxylate 在 水 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以1.05 g的产率得到(3R,4R)-tert-butyl 3-((6-(allyl(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

  摘要：

  We report a fast N -> O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.009

文献信息

• High yielding allylation of a chiral secondary alcohol containing base sensitive functional groups
  作者：James M. Kraus、Hunter C. Gits、Richard B. Silverman

  DOI：10.1016/j.tetlet.2011.12.120

  日期：2012.3

  of selective inhibitors, but the method was limited at a key step of forming an allyl ether intermediate. Yields for this step were very inconsistent, and the presence of base sensitive functional groups limited the range of available methods for forming this ether bond. This work describes a novel application of palladium catalyzed decarboxylative allylation, consistently resulting in a 90% isolated

  基于手性吡咯烷支架的神经元一氧化氮合酶抑制剂显示出治疗某些神经退行性疾病的希望。我们最近报道了一系列选择性抑制剂的合成，但该方法受限于形成烯丙基醚中间体的关键步骤。这一步的产率非常不一致，并且碱敏感官能团的存在限制了形成这种醚键的可用方法的范围。这项工作描述了钯催化脱羧烯丙基化的新应用，始终产生 90% 的分离产率，这对于合成这种关键的后期中间体至关重要。我们还报告了烯丙基-叔丁基碳酸酯前体的新的定量产率和直接合成。
• An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application
  作者：Fengtian Xue、Richard B. Silverman

  DOI：10.1016/j.tetlet.2010.03.009

  日期：2010.5

  We report a fast N -> O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state. (C) 2010 Elsevier Ltd. All rights reserved.