A Reductive Amination Using Methyl Esters as Nominal Electrophiles
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. The...
| Main Author: | |
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| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2023
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| Online Access: | https://eprints.nottingham.ac.uk/71958/ |
| _version_ | 1848800705188462592 |
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| author | Crooks, Jamie |
| author_facet | Crooks, Jamie |
| author_sort | Crooks, Jamie |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T20:55:48Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-71958 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:55:48Z |
| publishDate | 2023 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-719582023-09-13T12:05:07Z https://eprints.nottingham.ac.uk/71958/ A Reductive Amination Using Methyl Esters as Nominal Electrophiles Crooks, Jamie 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. 2023-07-26 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/71958/1/Thesis%20JC..pdf Crooks, Jamie (2023) A Reductive Amination Using Methyl Esters as Nominal Electrophiles. MRes thesis, University of Nottingham. amines organic chemistry synthesis |
| spellingShingle | amines organic chemistry synthesis Crooks, Jamie A Reductive Amination Using Methyl Esters as Nominal Electrophiles |
| title | A Reductive Amination Using Methyl Esters as Nominal Electrophiles |
| title_full | A Reductive Amination Using Methyl Esters as Nominal Electrophiles |
| title_fullStr | A Reductive Amination Using Methyl Esters as Nominal Electrophiles |
| title_full_unstemmed | A Reductive Amination Using Methyl Esters as Nominal Electrophiles |
| title_short | A Reductive Amination Using Methyl Esters as Nominal Electrophiles |
| title_sort | reductive amination using methyl esters as nominal electrophiles |
| topic | amines organic chemistry synthesis |
| url | https://eprints.nottingham.ac.uk/71958/ |