A Reductive Amination Using Methyl Esters as Nominal Electrophiles

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

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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: Thesis (University of Nottingham only) (MRes)
Supervisors: Denton, Ross
Keywords: amines, organic chemistry synthesis
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 71958
Depositing User: Crooks, Jamie
Date Deposited: 13 Sep 2023 12:05
Last Modified: 13 Sep 2023 12:05
URI: https://eprints.nottingham.ac.uk/id/eprint/71958

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