(3S,4R)-4-methylbenzyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate | 895577-97-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R)-4-methylbenzyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate
• 英文别名: (4-methylphenyl)methyl (3S,4R)-3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 895577-97-6
• 化学式: C₁₅H₂₀FNO₃
• 分子量: 281.327
• InChiKey: UBYPLVKUXKIITH-ZIAGYGMSSA-N

物化性质

• 沸点：
  418.9±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-methylbenzyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate 在 三氟甲磺酸酐 、 N,N-二异丙基乙胺 、 氨 、 水 、 盐酸 作用下， 以 乙腈 、 甲醇 、 甲苯 为溶剂， 反应 1.0h， 以82%的产率得到(3S,4R)-4-methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-1-carboxylate hydrochloride
  参考文献：
  名称：

  WO2006/69287

  摘要：

  公开号：
• 作为产物：
  描述：

  3-氟吡啶 在 盐酸 、 sodium tetrahydroborate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 Walphos SL-W003-1 、 palladium 10% on activated carbon 、 水 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -65.0~50.0 ℃ 、2.0 MPa 条件下， 反应 83.0h， 生成 (3S,4R)-4-methylbenzyl 3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  [EN] BICYCLIC AZAHETEROCYCLIC COMPOUNDS AS NR2B NMDA RECEPTOR ANTAGONISTS
  [FR] COMPOSÉS AZAHÉTÉROCYCLIQUES BICYCLIQUES UTILISÉS COMME ANTAGONISTES DES RÉCEPTEURS NMDA NR2B

  摘要：

  公开号：

  WO2016100349A3

文献信息

• [EN] TREATMENT OF ANXIETY DISORDERS AND AUTISM SPECTRUM DISORDERS<br/>[FR] TRAITEMENT DES TROUBLES DE L'ANXIÉTÉ ET DES TROUBLES DU SPECTRE AUTISTIQUE
  申请人：RUGEN HOLDINGS CAYMAN LTD

  公开号：WO2016049048A1

  公开（公告）日：2016-03-31

  Disclosed are methods for treating autism spectrum disorders and/or anxiety disorders by administering certain NR2B subunit-selective NMDA (N methyl-D aspartate) antagonists. Anxiety disorders include agoraphobia (with or without panic disorder), generalized anxiety disorder (GAD), social anxiety disorder (SAD), panic disorder (PD), post-traumatic stress disorder (PTSD) and obsessive-compulsive disorder (OCD).

  本文披露了通过给予特定NR2B亚单位选择性NMDA（N-甲基-D-天冬氨酸）拮抗剂来治疗自闭症谱系障碍和/或焦虑障碍的方法。焦虑障碍包括广场恐惧症（伴有或不伴有惊恐障碍）、广泛性焦虑障碍（GAD）、社交焦虑障碍（SAD）、惊恐障碍（PD）、创伤后应激障碍（PTSD）和强迫症（OCD）。
• Compounds, compositions and methods
  申请人：Cerecor, Inc.

  公开号：US10202363B2

  公开（公告）日：2019-02-12

  The disclosed subject matter provides certain polymorphic forms of Compound (I) as well as pharmaceutical compositions comprising Compound (I) or such polymorphic forms, and methods of using or making such compounds and pharmaceutical compositions. It has now been discovered that Compound (I) can exist in multiple crystalline forms (polymorphs). One particular crystalline form, Form II, has been found to be more thermodynamically stable and, thus, likely more suitable for bulk preparation and handling than other polymorphic forms. Efficient and economic methods have been developed to prepare Compound (I) and Form II in high purity on a large scale. In animal studies, Form II has demonstrated safety and efficacy in treating depressive disorders and, when micronized, improved absorption compared to non-micronized Form II.

  所公开的主题提供了化合物 (I) 的某些多晶型以及包含化合物 (I) 或此类多晶型的药物组合物，以及使用或制造此类化合物和药物组合物的方法。现已发现，化合物（I）可以多种结晶形式（多晶型）存在。其中一种特殊的结晶形态，即形态 II，已被发现在热力学上更为稳定，因此可能比其他多晶形态更适合批量制备和处理。目前已开发出高效、经济的方法来大规模制备高纯度的化合物 (I) 和形式 II。在动物实验中，形式 II 在治疗抑郁障碍方面具有安全性和有效性，与非微粉化形式 II 相比，微粉化形式 II 的吸收率更高。
• Process for Making Substituted Piperidines
  申请人：Nelson D. Todd

  公开号：US20080086006A1

  公开（公告）日：2008-04-10

  The present invention provides a process for the preparation of substituted piperidines which comprises an asymmetric hydrogenation of vinyl fluoride in the presence of a metal precursor complexed with a chiral mono- or biphosphine ligand.
• COMPOUNDS, COMPOSITIONS AND METHODS
  申请人：Cerecor, Inc.

  公开号：US20170369469A1

  公开（公告）日：2017-12-28

  The disclosed subject matter provides certain polymorphic forms of Compound (I) as well as pharmaceutical compositions comprising Compound (I) or such polymorphic forms, and methods of using or making such compounds and pharmaceutical compositions. It has now been discovered that Compound (I) can exist in multiple crystalline forms (polymorphs). One particular crystalline form, Form II, has been found to be more thermodynamically stable and, thus, likely more suitable for bulk preparation and handling than other polymorphic forms. Efficient and economic methods have been developed to prepare Compound (I) and Form II in high purity on a large scale. In animal studies, Form II has demonstrated safety and efficacy in treating depressive disorders and, when micronized, improved absorption compared to non-micronized Form II.
• TREATMENT OF ANXIETY DISORDERS AND AUTISM SPECTRUM DISORDERS
  申请人：LIU Jie

  公开号：US20180271869A1

  公开（公告）日：2018-09-27

  Disclosed are methods for treating autism spectrum disorders and/or anxiety disorders by administering certain NR2B subunit-selective NMDA (N methyl-D aspartate) antagonists. Anxiety disorders include agoraphobia (with or without panic disorder), generalized anxiety disorder (GAD), social anxiety disorder (SAD), panic disorder (PD), post-traumatic stress disorder (PTSD) and obsessive-compulsive disorder (OCD).