2,2-Dimethylpropanoyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate | 173526-47-1

• 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: 2,2-Dimethylpropanoyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 173526-47-1
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: ZSROYEAIRKBBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-Dimethylpropanoyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 在 碳酸氢钠 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (4S)-4-benzyl-3-[(2Z)-2-phenyl-2-piperidin-2-ylideneacetyl]-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
• 作为产物：
  描述：

  Boc-5-氨基戊酸 、 三甲基乙酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以100%的产率得到2,2-Dimethylpropanoyl 5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
  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

• Lithium-Initiated Imide Formation. A Simple Method for N-Acylation of 2-Oxazolidinones and Bornane-2,10-Sultam
  作者：Guo-Jie Ho、David J. Mathre

  DOI：10.1021/jo00112a060

  日期：1995.4
• 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.