A Reductive Amination Using Methyl Esters as Nominal ElectrophilesTools Crooks, Jamie (2023) A Reductive Amination Using Methyl Esters as Nominal Electrophiles. MRes thesis, University of Nottingham.
AbstractThis 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.
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