(R)-1-(3-aMino-4-(benzyloxy)phenyl)-2-(((R)-1-(4-Methoxyphenyl)propan-2-yl)aMino)ethanol | 299964-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(3-aMino-4-(benzyloxy)phenyl)-2-(((R)-1-(4-Methoxyphenyl)propan-2-yl)aMino)ethanol
• 英文别名: (1R)-1-(3-amino-4-phenylmethoxyphenyl)-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethanol
• CAS: 299964-43-5
• 化学式: C₂₅H₃₀N₂O₃
• 分子量: 406.525
• InChiKey: SFADXYACQOYZFR-KOSHJBKYSA-N

物化性质

• 沸点：
  612.8±55.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-(3-aMino-4-(benzyloxy)phenyl)-2-(((R)-1-(4-Methoxyphenyl)propan-2-yl)aMino)ethanol 在 10% palladium on active carbon 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 福莫特罗
  参考文献：
  名称：

  An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

  摘要：

  0The potent beta(2)-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00238-x
• 作为产物：
  描述：

  3'-硝基-4'-苄氧基-2-溴苯乙酮 在 盐酸 、 aluminum oxide 、 硼烷四氢呋喃络合物 、 铁粉 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 162.25h， 生成 (R)-1-(3-aMino-4-(benzyloxy)phenyl)-2-(((R)-1-(4-Methoxyphenyl)propan-2-yl)aMino)ethanol
  参考文献：
  名称：

  An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

  摘要：

  0The potent beta(2)-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00238-x

文献信息

• An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases
  作者：Francisco Campos、M.Pilar Bosch、Angel Guerrero

  DOI：10.1016/s0957-4166(00)00238-x

  日期：2000.7

  0The potent beta(2)-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. (C) 2000 Elsevier Science Ltd. All rights reserved.