tert-butyl (R,R,R)-2-hydroxy-3-[N-methyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate | 1346555-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (R,R,R)-2-hydroxy-3-[N-methyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate
• 英文别名: tert-butyl (2R,3R)-2-hydroxy-3-[[(1R)-1-(4-methoxyphenyl)ethyl]-methylamino]butanoate
• CAS: 1346555-91-6
• 化学式: C₁₈H₂₉NO₄
• 分子量: 323.433
• InChiKey: QSIKPUINNMPFHL-XJKCOSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (R,R,R)-2-hydroxy-3-[N-methyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate 在 正丁基锂 、 碘 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 69.5h， 生成 (2R,3S,4S,5R)-N(1)-methyl-2-acetoxy-3-(4'-methoxyphenyl)-4-O-methoxymethyl-5-methylpyrrolidine
  参考文献：
  名称：

  Asymmetric synthesis of (−)-codonopsinine

  摘要：

  The asymmetric synthesis of (-)-codonopsinine was achieved in 7 steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. The key step in this synthesis involved ring-closing iodoamination of a functionalised homoallylic amine, which occurred with concomitant N-debenzylation, to give a 3-iodopyrrolidine that was elaborated to (-)-codonopsinine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.114
• 作为产物：
  描述：

  巴豆酸叔丁酯 、 4-methoxy-N,α(αR)-dimethylbenzenemethylamine 在 正丁基锂 、 (1R)-(−)-(10-camphorsulfonyl)oxaziridine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.5h， 以71%的产率得到tert-butyl (R,R,R)-2-hydroxy-3-[N-methyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate
  参考文献：
  名称：

  Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine

  摘要：

  Ring-closing iodoamination of (E)-configured, N-alpha-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with 12 and NaHCO3 in MeCN occurs with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.045

文献信息

• Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine
  作者：Stephen G. Davies、James A. Lee、Paul M. Roberts、James E. Thomson、Callum J. West

  DOI：10.1016/j.tet.2012.03.045

  日期：2012.6

  Ring-closing iodoamination of (E)-configured, N-alpha-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with 12 and NaHCO3 in MeCN occurs with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. (c) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of (−)-codonopsinine
  作者：Stephen G. Davies、James A. Lee、Paul M. Roberts、James E. Thomson、Callum J. West

  DOI：10.1016/j.tetlet.2011.09.114

  日期：2011.11

  The asymmetric synthesis of (-)-codonopsinine was achieved in 7 steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. The key step in this synthesis involved ring-closing iodoamination of a functionalised homoallylic amine, which occurred with concomitant N-debenzylation, to give a 3-iodopyrrolidine that was elaborated to (-)-codonopsinine. (C) 2011 Elsevier Ltd. All rights reserved.