(4R,5S)-4-(4-methoxyphenyl)-5-pyridin-2-ylpyrrolidin-2-one | 200629-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4R,5S)-4-(4-methoxyphenyl)-5-pyridin-2-ylpyrrolidin-2-one
• CAS: 200629-39-6
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: YBWBIXISXCYOCC-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-(4-methoxyphenyl)-5-pyridin-2-ylpyrrolidin-2-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (2S,3R)-2-(pyridin-2-yl)-3-(4-methoxyphenyl)pyrrolidine
  参考文献：
  名称：

  Practical Synthesis of an Enantiomerically Pure trans-4,5-Disubstituted 2-Pyrrolidinone via Enzymatic Resolution. Preparation of the LTB₄ Inhibitor BIRZ-227

  摘要：

  A practical synthesis of the enantiomerically pure BIRZ-227 (1), a,LTB4 inhibitor, has been developed. The key steps include the effective synthesis of the trans-diarylpyrrolidinone (+/-)-8 and the enzymatic resolution of N-acetoxymethyl pyrrolidinone (+/-)-10 by immobilized Lipase Novozym 435. Reduction of pyrrolidinone (+)-8 with borane and subsequent coupling with chlorobenzoxazole 2 furnished BIRZ-227 in high enantiomeric purity (99% ee). The overall process described herein required no chromatographic separation and is amenable to the preparation of multikilogram quantities of the desired drug candidate in a cost-effective manner.

  DOI：

  10.1021/jo971605p
• 作为产物：
  描述：

  1,1-diphenyl-N-(pyridin-2-ylmethyl)methanimine 在 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 苄基三甲基氯化铵 、 三乙胺 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 85.0h， 生成 (4R,5S)-4-(4-methoxyphenyl)-5-pyridin-2-ylpyrrolidin-2-one
  参考文献：
  名称：

  Practical Synthesis of an Enantiomerically Pure trans-4,5-Disubstituted 2-Pyrrolidinone via Enzymatic Resolution. Preparation of the LTB₄ Inhibitor BIRZ-227

  摘要：

  A practical synthesis of the enantiomerically pure BIRZ-227 (1), a,LTB4 inhibitor, has been developed. The key steps include the effective synthesis of the trans-diarylpyrrolidinone (+/-)-8 and the enzymatic resolution of N-acetoxymethyl pyrrolidinone (+/-)-10 by immobilized Lipase Novozym 435. Reduction of pyrrolidinone (+)-8 with borane and subsequent coupling with chlorobenzoxazole 2 furnished BIRZ-227 in high enantiomeric purity (99% ee). The overall process described herein required no chromatographic separation and is amenable to the preparation of multikilogram quantities of the desired drug candidate in a cost-effective manner.

  DOI：

  10.1021/jo971605p

文献信息

• A practical one-pot synthesis of trans-4,5-disubstituted 2-pyrrolidinones and the related pyrrolidines
  作者：Nathan K. Yee

  DOI：10.1016/s0040-4039(97)01134-9

  日期：1997.7

  A practical and general method for the stereoselective synthesis of trans-4,5-disubstituted 2-pyrrolidinones was developed. Hydride reduction of these pyrrolidinones gave the corresponding pyrrolidines. (C) 1997 Elsevier Science Ltd.
• Practical Synthesis of an Enantiomerically Pure <i>trans-</i>4,5-Disubstituted 2-Pyrrolidinone via Enzymatic Resolution. Preparation of the LTB₄ Inhibitor BIRZ-227
  作者：Nathan K. Yee、Laurence J. Nummy、Denis P. Byrne、Lana L. Smith、Gregory P. Roth

  DOI：10.1021/jo971605p

  日期：1998.1.1

  A practical synthesis of the enantiomerically pure BIRZ-227 (1), a,LTB4 inhibitor, has been developed. The key steps include the effective synthesis of the trans-diarylpyrrolidinone (+/-)-8 and the enzymatic resolution of N-acetoxymethyl pyrrolidinone (+/-)-10 by immobilized Lipase Novozym 435. Reduction of pyrrolidinone (+)-8 with borane and subsequent coupling with chlorobenzoxazole 2 furnished BIRZ-227 in high enantiomeric purity (99% ee). The overall process described herein required no chromatographic separation and is amenable to the preparation of multikilogram quantities of the desired drug candidate in a cost-effective manner.