tert-butyl (2S,4R)-2-[benzyl(methyl)carbamoyl]-4-hydroxypyrrolidine-1-carboxylate | 330583-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S,4R)-2-[benzyl(methyl)carbamoyl]-4-hydroxypyrrolidine-1-carboxylate
• CAS: 330583-66-9
• 化学式: C₁₈H₂₆N₂O₄
• 分子量: 334.415
• InChiKey: KOZYUHXNVJRXHG-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4R)-2-[benzyl(methyl)carbamoyl]-4-hydroxypyrrolidine-1-carboxylate 在 lithium aluminium tetrahydride 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-benzyl-N-methyl-1-[(2S,4R)-1-methyl-4-prop-2-enoxypyrrolidin-2-yl]methanamine
  参考文献：
  名称：

  A Polymer-Supported Proline-Based Diamine Catalyst for the Kinetic Resolution of Racemic Secondary Alcohols

  摘要：

  The preparation of polymer-supported proline-based diamine catalyst 12 for the kinetic resolution of racemic mixtures of secondary alcohols is described. Not only is the catalyst effective for the resolution of a host of different alcohols, it can also be recovered and reused several times without loss of either activity or selectivity. The catalyst has been used in conjunction with a polymer-supported sequestration strategy, giving rise to an essentially pure mixture of resolved products that can be separated using flash chromatography.

  DOI：

  10.1021/jo0013610
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 、 N-甲基苄胺 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以98%的产率得到tert-butyl (2S,4R)-2-[benzyl(methyl)carbamoyl]-4-hydroxypyrrolidine-1-carboxylate
  参考文献：
  名称：

  A Polymer-Supported Proline-Based Diamine Catalyst for the Kinetic Resolution of Racemic Secondary Alcohols

  摘要：

  The preparation of polymer-supported proline-based diamine catalyst 12 for the kinetic resolution of racemic mixtures of secondary alcohols is described. Not only is the catalyst effective for the resolution of a host of different alcohols, it can also be recovered and reused several times without loss of either activity or selectivity. The catalyst has been used in conjunction with a polymer-supported sequestration strategy, giving rise to an essentially pure mixture of resolved products that can be separated using flash chromatography.

  DOI：

  10.1021/jo0013610

文献信息

• A Polymer-Supported Proline-Based Diamine Catalyst for the Kinetic Resolution of Racemic Secondary Alcohols
  作者：Bruce Clapham、Chang-Woo Cho、Kim D. Janda

  DOI：10.1021/jo0013610

  日期：2001.2.1

  The preparation of polymer-supported proline-based diamine catalyst 12 for the kinetic resolution of racemic mixtures of secondary alcohols is described. Not only is the catalyst effective for the resolution of a host of different alcohols, it can also be recovered and reused several times without loss of either activity or selectivity. The catalyst has been used in conjunction with a polymer-supported sequestration strategy, giving rise to an essentially pure mixture of resolved products that can be separated using flash chromatography.