ethyl 3-amino-3-(4-(benzyloxy)phenyl)propanoate | 1246513-83-6

• 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: ethyl 3-amino-3-(4-(benzyloxy)phenyl)propanoate
• 英文别名: ethyl (3S)-3-amino-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 1246513-83-6
• 化学式: C₁₈H₂₁NO₃
• mdl: MFCD05861425
• 分子量: 299.37
• InChiKey: CNUONIQYWHGUDA-KRWDZBQOSA-N

物化性质

• 沸点：
  445.1±45.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-3-(4-(benzyloxy)phenyl)propanoate 在 咪唑 、 乙酰丙酮 、 对溴氟苯 、 copper(l) chloride 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 以82%的产率得到ethyl 4-benzyloxycinnamate
  参考文献：
  名称：

  Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe

  摘要：

  Two routes for the preparation of an N-aryl beta-amino acid, an important precursor for the cholesterol-lowering drug Ezetimibe, were investigated. The first pathway proceeds via an Rh- or Ir-catalyzed asymmetric hydrogenation of N-aryl enamine giving the desired product with up to 82% ee. The other pathway involves a direct asymmetric reductive amination (DARA) of the beta-keto ester which yielded the beta-amino ester in high yield and 97% ee. Subsequent copper-catalyzed N-arylation gave the target compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.013
• 作为产物：
  描述：

  ethyl 3-[4-(benzyloxy)phenyl]-3-oxopropanoate 在 dimethylammonium dichlorotri(μ-chloro)bis[(R)-(+)-5,5'-bis[di(3,5-xylyl)phosphino]-4,4'-bi-1,3-benzodioxole]diruthenate(II) 、 氢气 、 2-羟基苯甲酸单铵盐 、 水杨酸 作用下， 以 乙醇 为溶剂， 85.0 ℃ 、5.0 MPa 条件下， 反应 10.0h， 以80%的产率得到ethyl 3-amino-3-(4-(benzyloxy)phenyl)propanoate
  参考文献：
  名称：

  Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe

  摘要：

  Two routes for the preparation of an N-aryl beta-amino acid, an important precursor for the cholesterol-lowering drug Ezetimibe, were investigated. The first pathway proceeds via an Rh- or Ir-catalyzed asymmetric hydrogenation of N-aryl enamine giving the desired product with up to 82% ee. The other pathway involves a direct asymmetric reductive amination (DARA) of the beta-keto ester which yielded the beta-amino ester in high yield and 97% ee. Subsequent copper-catalyzed N-arylation gave the target compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.013

文献信息

• Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe
  作者：Guuske F. Busscher、Laurent Lefort、Jozef G.O. Cremers、Marco Mottinelli、Roel W. Wiertz、Ben de Lange、Yutaka Okamura、Yukinori Yusa、Kazuhiko Matsumura、Hideo Shimizu、Johannes G. de Vries、André H.M. de Vries

  DOI：10.1016/j.tetasy.2010.04.013

  日期：2010.7

  Two routes for the preparation of an N-aryl beta-amino acid, an important precursor for the cholesterol-lowering drug Ezetimibe, were investigated. The first pathway proceeds via an Rh- or Ir-catalyzed asymmetric hydrogenation of N-aryl enamine giving the desired product with up to 82% ee. The other pathway involves a direct asymmetric reductive amination (DARA) of the beta-keto ester which yielded the beta-amino ester in high yield and 97% ee. Subsequent copper-catalyzed N-arylation gave the target compound. (C) 2010 Elsevier Ltd. All rights reserved.