(3SR,4SR)-1-(4-fluorobenzyl)-4-(tert-butylamino)piperidin-3-ol

• 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: (3SR,4SR)-1-(4-fluorobenzyl)-4-(tert-butylamino)piperidin-3-ol
• 英文别名: (3S,4S)-4-(tert-butylamino)-1-[(4-fluorophenyl)methyl]piperidin-3-ol
• 化学式: C₁₆H₂₅FN₂O
• 分子量: 280.386
• InChiKey: YQRBRVJQTPGWNS-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4'-fluorobenzyl)pyridinium chloride 在 sodium tetrahydroborate 、 三氟乙酸 、 lithium bromide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 44.5h， 生成 (3SR,4SR)-1-(4-fluorobenzyl)-4-(tert-butylamino)piperidin-3-ol
  参考文献：
  名称：

  High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines

  摘要：

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.045

文献信息

• High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines
  作者：Matthias Scheunemann、Lothar Hennig、Uta Funke、Jörg Steinbach

  DOI：10.1016/j.tet.2011.03.045

  日期：2011.5

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.