A Reductive Amination Using Methyl Esters as Nominal Electrophiles
Publication Date
July 26, 2023
Creator
Abstract
This report investigates a one-pot catalytic domino reaction for the synthesis of amines from methyl esters. The first step is a 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) catalysed amidation immediately followed by a zinc acetate catalysed reduction using phenyl silane as the terminal reductant. These conditions were then used to successfully synthesis 11 tertiary amines with yields ranging from 40 % to 92 %, and nine secondary amines with yieldsranging from 23 % to 81 %. Both primary and secondary amines were investigated along with a range of different methyl esters which allowed us to investigate the versatility of the substrate scope. The reaction is then exemplified through the synthesis of active pharmaceuticals Piribedil and Cinacalcet.
Item Type
ethesis
Thesis Type
MRes
Supervisors
Keywords
Subjects (LC)
Associated Schools / Departments
School of Chemistry
eprints ID
71958
UoN Repository URI
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Thesis JC..pdf
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Full-text
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