(3S)-tert-butyl 3-(4-fluorobenzyl)piperidine-1-carboxylate | 745815-12-7

• 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: (3S)-tert-butyl 3-(4-fluorobenzyl)piperidine-1-carboxylate
• 英文别名: tert-butyl (3S)-3-[(4-fluorophenyl)methyl]piperidine-1-carboxylate
• CAS: 745815-12-7
• 化学式: C₁₇H₂₄FNO₂
• 分子量: 293.381
• InChiKey: VISNTYBUDIDKRV-AWEZNQCLSA-N

物化性质

• 沸点：
  374.3±15.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-tert-butyl 3-(4-fluorobenzyl)piperidine-1-carboxylate 在 盐酸 、 三乙酰氧基硼氢化钠 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Discovery of N-propylurea 3-benzylpiperidines as selective CC chemokine receptor-3 (CCR3) antagonists

  摘要：

  The discovery of novel and selective small molecule antagonists of the CC Chemokine Receptor-3 (CCR3) is presented. Simple conversion from a 4- to 3-benzylpiperidine gave improved selectivity for CCR3 over the serotonin 5HT(2A) receptor. Chiral resolution and exploration of mono- and disubstitution of the N-propylurea resulted in several 3-benzylpiperidine N-propylureas with CCR3 binding IC50S under 5 nM. Data from in vitro calcium mobilization and chemotaxis assays for these compounds ranged from high picomolar to low nanomolar EC(50)s and correlated well with antagonist binding IC(50)s. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.059
• 作为产物：
  描述：

  N-BOC-3-羟基哌啶 在 palladium on activated charcoal 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， -78.0 ℃ 、275.79 kPa 条件下， 反应 13.0h， 生成 (3S)-tert-butyl 3-(4-fluorobenzyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery of N-propylurea 3-benzylpiperidines as selective CC chemokine receptor-3 (CCR3) antagonists

  摘要：

  The discovery of novel and selective small molecule antagonists of the CC Chemokine Receptor-3 (CCR3) is presented. Simple conversion from a 4- to 3-benzylpiperidine gave improved selectivity for CCR3 over the serotonin 5HT(2A) receptor. Chiral resolution and exploration of mono- and disubstitution of the N-propylurea resulted in several 3-benzylpiperidine N-propylureas with CCR3 binding IC50S under 5 nM. Data from in vitro calcium mobilization and chemotaxis assays for these compounds ranged from high picomolar to low nanomolar EC(50)s and correlated well with antagonist binding IC(50)s. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.059

文献信息

• Efficient Preparation of (3<i>S</i>)-3-(4-Fluorobenzyl)piperidinium Mandelate
  作者：Dean Wacker、George Emmett、Gary Cain、Melissa Estrella、Edd Holler、James Piecara、Andrew Blum、Alfred Mical、Christopher Teleha

  DOI：10.1055/s-2004-834903

  日期：——

  Methods for the preparation of (3S)-3-(4-fluorobenzyl)piperidine (2) and its mandelate salt (9) are described. The first generation synthesis started from 3-benzylpiperidone, and required Boc protection of the nitrogen for efficient separation of the enantiomers using chromatography on a chiral stationary phase. Subsequently, a resolution method using (R)-mandelic acid, produced high %ee salt 9 after

  描述了制备(3S)-3-(4-氟苄基)哌啶(2)及其扁桃酸盐(9)的方法。第一代合成从 3-苄基哌啶酮开始，需要 Boc 保护氮，以便在手性固定相上使用色谱法有效分离对映异构体。随后，使用 (R)-扁桃酸的拆分方法，在重结晶后产生了高 %ee 盐 9，并且无需 Boc 保护。第三代路线，从吡啶-3-甲醛开始，导致外消旋体 2 的流线型合成，并针对生产数百克手性盐进行了优化。
• O-GLYCOPROTEIN-2-ACETAMIDO-2-DEOXY-3-D-GLYCOPYRANOSIDASE INHIBITORS
  申请人：Biogen MA Inc.

  公开号：EP3765458A1

  公开（公告）日：2021-01-20
• [EN] O-GLYCOPROTEIN-2-ACETAMIDO-2-DEOXY-3-D-GLYCOPYRANOSIDASE INHIBITORS<br/>[FR] INHIBITEURS D'O-GLYCOPROTÉINE-2-ACÉTAMIDO-2-DÉSOXY-3-D-GLYCOPYRANOSIDASE
  申请人：BIOGEN MA INC

  公开号：WO2019178191A1

  公开（公告）日：2019-09-19

  Described herein are compounds represented by formula (I") or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising the same and methods of preparing and using the same. The variables Ar, Ra, Rb, m, n, Y1, Y2, R3 and R4 are defined herein.
• Discovery of N-propylurea 3-benzylpiperidines as selective CC chemokine receptor-3 (CCR3) antagonists
  作者：Jeffrey G Varnes、Daniel S Gardner、Joseph B Santella、John V Duncia、Melissa Estrella、Paul S Watson、Cheryl M Clark、Soo S Ko、Patricia Welch、Maryanne Covington、Nicole Stowell、Eric Wadman、Paul Davies、Kimberley Solomon、Robert C Newton、George L Trainor、Carl P Decicco、Dean A Wacker

  DOI：10.1016/j.bmcl.2004.01.059

  日期：2004.4

  The discovery of novel and selective small molecule antagonists of the CC Chemokine Receptor-3 (CCR3) is presented. Simple conversion from a 4- to 3-benzylpiperidine gave improved selectivity for CCR3 over the serotonin 5HT(2A) receptor. Chiral resolution and exploration of mono- and disubstitution of the N-propylurea resulted in several 3-benzylpiperidine N-propylureas with CCR3 binding IC50S under 5 nM. Data from in vitro calcium mobilization and chemotaxis assays for these compounds ranged from high picomolar to low nanomolar EC(50)s and correlated well with antagonist binding IC(50)s. (C) 2004 Elsevier Ltd. All rights reserved.