(4S)-4-benzyl-3-[(2S)-2-phenyl-2-[(2R)-piperidin-2-yl]acetyl]-1,3-oxazolidin-2-one | 253680-96-5

• 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: (4S)-4-benzyl-3-[(2S)-2-phenyl-2-[(2R)-piperidin-2-yl]acetyl]-1,3-oxazolidin-2-one
• CAS: 253680-96-5
• 化学式: C₂₃H₂₆N₂O₃
• 分子量: 378.471
• InChiKey: IFTISTQEASOGRG-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (4S)-4-benzyl-3-[(2S)-2-phenyl-2-[(2R)-piperidin-2-yl]acetyl]-1,3-oxazolidin-2-one 在 LnI₃ 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以85%的产率得到methyl (αS,2R)-phenyl-(piperidin-2-yl)acetate
  参考文献：
  名称：

  Enantioselective synthesis of (2S,2′R)-erythro-methylphenidate

  摘要：

  A new approach towards the enantioselective synthesis of (2S,2'R)-erythro-methylphenidate (1) is described. The key step in the synthesis utilizes Evans' 4-substituted-2-oxazolidinone chiral auxiliary to control the diastereofacial selectivity in the hydrogenation of enamine intermediate 6, yielding the hydrogenated product 7 with excellent diastereoselectivity. Methanolysis of 7 afforded 1 with excellent enantiopurity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00384-5
• 作为产物：
  描述：

  (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone 在 palladium on activated charcoal 、 氢气 、 碳酸氢钠 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 (4S)-4-benzyl-3-[(2S)-2-phenyl-2-[(2R)-piperidin-2-yl]acetyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of (2S,2′R)-erythro-methylphenidate

  摘要：

  A new approach towards the enantioselective synthesis of (2S,2'R)-erythro-methylphenidate (1) is described. The key step in the synthesis utilizes Evans' 4-substituted-2-oxazolidinone chiral auxiliary to control the diastereofacial selectivity in the hydrogenation of enamine intermediate 6, yielding the hydrogenated product 7 with excellent diastereoselectivity. Methanolysis of 7 afforded 1 with excellent enantiopurity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00384-5

文献信息

• Enantioselective synthesis of (2S,2′R)-erythro-methylphenidate
  作者：Mahavir Prashad、Yugang Liu、Hong-Yong Kim、Oljan Repic、Thomas J Blacklock

  DOI：10.1016/s0957-4166(99)00384-5

  日期：1999.9

  A new approach towards the enantioselective synthesis of (2S,2'R)-erythro-methylphenidate (1) is described. The key step in the synthesis utilizes Evans' 4-substituted-2-oxazolidinone chiral auxiliary to control the diastereofacial selectivity in the hydrogenation of enamine intermediate 6, yielding the hydrogenated product 7 with excellent diastereoselectivity. Methanolysis of 7 afforded 1 with excellent enantiopurity. (C) 1999 Elsevier Science Ltd. All rights reserved.