反应 #586093

反应方程式

2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-ol

sodium hydride

methyl iodide

2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-ol

phenol

3-phenoxy-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane

2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-ol

triphenylphosphine

→

3-methoxy-2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octane

溶剂

ether

反应条件

后处理

1. 1
   其他results

实验过程

The saturated alcohol intermediates, such as 2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-ol, can also serve as templates for compound libraries. For instance, ethers can be generated from these alcohols, for example, using either Mitsunobu or Williamson conditions. Thus, by way of example, when 2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-ol is reacted with phenol via Mitsunobu coupling with diethylazidocarboxylate and triphenylphosphine (Guthrie et al., J. Chem. Soc., Perkin Trans I 45: 2328 (1981)), 3-phenoxy-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane results. Similarly, when 2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-ol is treated with sodium hydride and methyl iodide, the unsaturated ether, 3-methoxy-2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octane, is formed. This gives the saturated ether, 3-methoxy-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane (predominantly cis), upon catalytic hydrogenation.

来源