Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center.

doi:10.1021/JO0491758

Paper

Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center.

Published 2004 · Jun'ichi Uenishi, Masahiro Hamada, Sachiko Aburatani

The Journal of organic chemistry

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20

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Abstract

Stereospecific substitutions of optically pure 1-(pyridinyl)ethyl methanesulfonates with various amines are described. The reaction of (R)- or (S)-1-(2-pyridinyl)ethyl methanesulfonate with primary amines, including amino acid esters, gives N-substituted (S)- or (R)-1-(2-pyridinyl)ethylamines (4) with inversion of the configuration. Secondary cyclic amines are also reacted with (R)-2 to give the corresponding substituted amines (5) in excellent yields. Optically pure and meso triamine ligands having two pyridine rings, (S,S)-4f and meso-4f, (S,S)-9e, (S,R)-9e, and (S,S)-9f, have been prepared in stereochemically pure form by this method. Not only the substitution reaction of optically active 2 but also that of 1-(4-pyridinyl)ethyl and 1-(3-pyridinyl)ethyl methanesulfonates 11 and 14 take place stereospecifcally with inversion of the chiral center.

Study Snapshot

This study demonstrates a method for stereospecific substitution of 1-(2-pyridinyl)ethyl methanesulfonates with various amines, leading to N-substituted chiral nonracemic 1-(2-pyridinyl)ethylamines with

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center.

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