(3R,4R)-4-aminopiperidin-3-ol | 1007596-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R)-4-aminopiperidin-3-ol
• CAS: 1007596-94-2
• 化学式: C₅H₁₂N₂O
• 分子量: 116.163
• InChiKey: UVBKPWNFXFUDOU-RFZPGFLSSA-N

物化性质

• 沸点：
  221.9±40.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-aminopiperidin-3-ol 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 异丙醇 、 甲苯 为溶剂， 50.0~75.0 ℃ 、13.33 kPa 条件下， 反应 4.5h， 生成
  参考文献：
  名称：

  Evolution of the Process for the Preparation of a Selective ErbB VEGF Receptor Inhibitor

  摘要：

  An efficient synthetic route to the potent and selective ErbB VEGF receptor inhibitor, BMS-690514 (1) is described. Strategic modifications in both approach and procedure addressed several issues, which led to a safe, efficient, and economical process for the preparation of multi-kilogram quantities of 1. The convergent route involves alkylation of a suitably protected (3R,4R)-4-aminopiperidin-3-ol with the triethyl(alkyl) ammonium salt of a functionalized pyrrolotriazine 3a followed by deprotection to provide 1 as the crystalline free base.

  DOI：

  10.1055/s-0032-1317540
• 作为产物：
  描述：

  (3S,7aR)-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one 在 苯甲砜 、 氢气 、 palladium(II) hydroxide 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 35.0~110.0 ℃ 、308.18 kPa 条件下， 生成 (3R,4R)-4-aminopiperidin-3-ol
  参考文献：
  名称：

  Evolution of the Process for the Preparation of a Selective ErbB VEGF Receptor Inhibitor

  摘要：

  An efficient synthetic route to the potent and selective ErbB VEGF receptor inhibitor, BMS-690514 (1) is described. Strategic modifications in both approach and procedure addressed several issues, which led to a safe, efficient, and economical process for the preparation of multi-kilogram quantities of 1. The convergent route involves alkylation of a suitably protected (3R,4R)-4-aminopiperidin-3-ol with the triethyl(alkyl) ammonium salt of a functionalized pyrrolotriazine 3a followed by deprotection to provide 1 as the crystalline free base.

  DOI：

  10.1055/s-0032-1317540

文献信息

• PROCESS FOR PRODUCING 1-SUBSTITUTED TRANS-4-(SUBSTITUTED AMINO) PIPERIDIN-3-OL
  申请人：Aikawa Toshiaki

  公开号：US20110172431A1

  公开（公告）日：2011-07-14

  A process is provided for producing a 1-substituted trans-4-(substituted amino)piperidin-3-ol represented by formula (III-1): The process includes a step of reacting a 1-substituted-3,4-epoxypiperidine represented by formula (I): with an amine compound represented by formula (II) in the presence of an inorganic lithium salt. By utilizing the process, trans-4-aminopiperidin-3-ol compounds useful as various chemical products, such as medicine intermediates, can be produced.

  提供了一种生产1-取代的反式-4-(取代氨基)哌啶-3-醇的过程，其化学式为(III-1)：该过程包括以下步骤：将一种化学式为(I)的1-取代-3,4-环氧哌啶与一种化学式为(II)的胺化合物在无机锂盐存在下反应。通过利用该过程，可以生产用途广泛的反式-4-氨基哌啶-3-醇化合物，如药物中间体等化学产品。
• F<scp>ragtory</scp>: Pharmacophore-Focused Design, Synthesis, and Evaluation of an sp³-Enriched Fragment Library
  作者：Mike Bührmann、Shivakrishna Kallepu、Jonas D. Warmuth、Jan N. Wiese、Christiane Ehrt、Helge Vatheuer、Wolf Hiller、Carina Seitz、Laura Levy、Paul Czodrowski、Sonja Sievers、Matthias P. Müller、Daniel Rauh

  DOI：10.1021/acs.jmedchem.3c00187

  日期：2023.5.11

  structures in commercial libraries often hamper the full potential of this approach. Hence, the thorough design of screening libraries inevitably determines the probability for meaningful hits and subsequent structural elaboration. Against this background, we present the generation of an exclusive fragment library based on iterative entry nomination by a specifically designed computational workflow:

  基于片段的药物发现在药物化学和药物研究中发挥了重要作用。尽管取得了许多成功，但商业文库中平面、sp 2丰富的结构的有限多样性和过度代表性往往阻碍了这种方法的全部潜力。因此，筛选文库的彻底设计不可避免地决定了有意义的命中和随后的结构阐述的概率。在此背景下，我们通过专门设计的计算工作流程“ Fragtory ”，提出了基于迭代条目提名的独家片段库的生成。遵循药效团多样性驱动的方法，我们使用了Fragtory在跨学科的学术环境中，指导定制合成工作和内部化合物的实施，以建立一个由 288 名成员组成的精选 sp 3片段库。随后针对模型蛋白质的核磁共振筛选和蛋白质晶体学的命中验证导致了结构新颖的配体的鉴定，这些配体通过等温滴定量热法进一步表征，证明了我们的实验方法的适用性。
• WO2008/20222
  申请人：——

  公开号：——

  公开（公告）日：——
• Evolution of the Process for the Preparation of a Selective ErbB VEGF Receptor Inhibitor
  作者：Boguslaw Mudryk、Amit Joshi、Adrian Ortiz、Ian Young、James Sawyer、Bin Zheng、Masano Sugiyama、Zhongping Shi、Jale Müslehiddinoğlu、R. Corbett、David Kronenthal、David Conlon

  DOI：10.1055/s-0032-1317540

  日期：——

  An efficient synthetic route to the potent and selective ErbB VEGF receptor inhibitor, BMS-690514 (1) is described. Strategic modifications in both approach and procedure addressed several issues, which led to a safe, efficient, and economical process for the preparation of multi-kilogram quantities of 1. The convergent route involves alkylation of a suitably protected (3R,4R)-4-aminopiperidin-3-ol with the triethyl(alkyl) ammonium salt of a functionalized pyrrolotriazine 3a followed by deprotection to provide 1 as the crystalline free base.