(3R,4R)-tert-butyl 3-{{6'-[benzyl(tert-butoxycarbonyl)amino]-4'-methylpyridin-2'-yl}methyl}-4-(3'-hydroxypropoxy)pyrrolidine-1-carboxylate | 1356133-68-0

• 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'-[benzyl(tert-butoxycarbonyl)amino]-4'-methylpyridin-2'-yl}methyl}-4-(3'-hydroxypropoxy)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3R,4R)-3-[[6-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-4-methylpyridin-2-yl]methyl]-4-(3-hydroxypropoxy)pyrrolidine-1-carboxylate
• CAS: 1356133-68-0
• 化学式: C₃₁H₄₅N₃O₆
• 分子量: 555.715
• InChiKey: SIJGHPNJAGIQHA-RSXGOPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4R)-tert-butyl 3-{{6'-[benzyl(tert-butoxycarbonyl)amino]-4'-methylpyridin-2'-yl}methyl}-4-(3'-hydroxypropoxy)pyrrolidine-1-carboxylate 在 20% palladium hydroxide on charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以65%的产率得到(3R,4R)-tert-butyl 3-{{6'-[(tert-butoxycarbonyl)amino]-4'-methylpyridin-2'-yl}methyl}-4-(3'-hydroxypropoxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Acid-facilitated debenzylation of N-Boc, N-benzyl double protected 2-aminopyridinomethyl pyrrolidine derivatives

  摘要：

  2-Aminopyridinomethyl pyrrolidines represent a class of highly potent and selective neuronal nitric oxide synthase inhibitors. Conditions for a Mitsunobu reaction of a naphthol and a hindered secondary alcohol were optimized to give good to excellent yields. A key step in the synthesis of these inhibitors is the deprotection of the benzyl group from the N-Boc and N-Bn double protected 2-aminopyridine ring at a late stage of the synthesis, which has been proven difficult in our previous syntheses. Acetic acid was found to facilitate the N-Bn deprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.013

文献信息

• Selective Neuronal Nitric Oxide Synthase Inhibitors
  申请人：Silverman Richard B.

  公开号：US20120258513A1

  公开（公告）日：2012-10-11

  Compounds and related methods for selective inhibition of neuronal nitric oxide synthase over inducible and endothelial isoforms, such compounds as can provide reduced cationic character and enhanced bioavailability.
• US8557552B2
  申请人：——

  公开号：US8557552B2

  公开（公告）日：2013-10-15