tert-butyl (3S,5S)-3-amino-5-(4-methoxyphenyl)piperidine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (3S,5S)-3-amino-5-(4-methoxyphenyl)piperidine-1-carboxylate
• 化学式: C₁₇H₂₆N₂O₃
• 分子量: 306.405
• InChiKey: FZDGKZWJEWNNEZ-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 18.0h， 以79%的产率得到tert-butyl (3S,5S)-3-amino-5-(4-methoxyphenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Remote Functionalization: Palladium-Catalyzed C5(sp³)-H Arylation of 1-Boc-3-aminopiperidine through the Use of a Bidentate Directing Group

  摘要：

  A protocol for the Pd-catalyzed CS(sp(3))-H arylation of readily available 1-Boc-3-(picolinoylamino)piperidine with iodo(hetero)arenes is reported. The substrate can be obtained from a biorenewable feedstock, namely L-arginine. The use of the right N1 protective group is decisive to get arylation. The addition of a catalytic amount of 2,6-dimethylbenzoic acid and performing the reaction at high concentration are important to achieve a high conversion and yield. The procedure gives arylated 1-Boc-3-(picolinoylamino)piperidines in a regiospecific (C5) and stereo-specific (cis) manner. Orthogonal cleavage of the amide over the carbamate group allows one to further selectively derivatize the amino moieties of the piperidine scaffold.

  DOI：

  10.1021/acscatal.6b00841

文献信息

• Remote Functionalization: Palladium-Catalyzed C5(sp³)-H Arylation of 1-Boc-3-aminopiperidine through the Use of a Bidentate Directing Group
  作者：Ben F. Van Steijvoort、Nadya Kaval、Artem A. Kulago、Bert U. W. Maes

  DOI：10.1021/acscatal.6b00841

  日期：2016.7.1

  A protocol for the Pd-catalyzed CS(sp(3))-H arylation of readily available 1-Boc-3-(picolinoylamino)piperidine with iodo(hetero)arenes is reported. The substrate can be obtained from a biorenewable feedstock, namely L-arginine. The use of the right N1 protective group is decisive to get arylation. The addition of a catalytic amount of 2,6-dimethylbenzoic acid and performing the reaction at high concentration are important to achieve a high conversion and yield. The procedure gives arylated 1-Boc-3-(picolinoylamino)piperidines in a regiospecific (C5) and stereo-specific (cis) manner. Orthogonal cleavage of the amide over the carbamate group allows one to further selectively derivatize the amino moieties of the piperidine scaffold.