Elucidation of some reactions of methyl 3-(benzyl(2-hydoxyethyl)amino)propionate using NMR

R Alan Aitken; Joseph D.D. Hunt

doi:10.1016/j.molstruc.2025.141411

Elucidation of some reactions of methyl 3-(benzyl(2-hydoxyethyl)amino)propionate using NMR

R Alan Aitken^*, Joseph D.D. Hunt

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Contrary to a literature report on a close analogue, reaction of methyl 3-(benzyl(2-hydroxyethyl)amino)propionate with methanesulfonyl chloride and triethylamine gives not the expected mesylate but the corresponding chloride. Conversion of the alcohol into the corresponding bromide was achieved using carbon tetrabromide and triphenylphosphine. Fully assigned ¹H and ¹³C NMR spectra are presented and compared for all three compounds.

Original language	English
Article number	141411
Number of pages	6
Journal	Journal of Molecular Structure
Volume	1328
Early online date	12 Jan 2025
DOIs	https://doi.org/10.1016/j.molstruc.2025.141411
Publication status	Published - 15 Jan 2025

Keywords

1H NMR
13C NMR
COSY
HSQC
HMBC

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10.1016/j.molstruc.2025.141411Licence: CC BY

Aitken_JMS_Elucidation-of-Some-Reactions_CCBY
© 2025 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY license. https://doi.org/10.1016/j.micromeso.2025.113502
Final published version, 580 KBLicence: CC BY

Cite this

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abstract = "Contrary to a literature report on a close analogue, reaction of methyl 3-(benzyl(2-hydroxyethyl)amino)propionate with methanesulfonyl chloride and triethylamine gives not the expected mesylate but the corresponding chloride. Conversion of the alcohol into the corresponding bromide was achieved using carbon tetrabromide and triphenylphosphine. Fully assigned 1H and 13C NMR spectra are presented and compared for all three compounds.",

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T1 - Elucidation of some reactions of methyl 3-(benzyl(2-hydoxyethyl)amino)propionate using NMR

AU - Aitken, R Alan

AU - Hunt, Joseph D.D.

PY - 2025/1/15

Y1 - 2025/1/15

N2 - Contrary to a literature report on a close analogue, reaction of methyl 3-(benzyl(2-hydroxyethyl)amino)propionate with methanesulfonyl chloride and triethylamine gives not the expected mesylate but the corresponding chloride. Conversion of the alcohol into the corresponding bromide was achieved using carbon tetrabromide and triphenylphosphine. Fully assigned 1H and 13C NMR spectra are presented and compared for all three compounds.

AB - Contrary to a literature report on a close analogue, reaction of methyl 3-(benzyl(2-hydroxyethyl)amino)propionate with methanesulfonyl chloride and triethylamine gives not the expected mesylate but the corresponding chloride. Conversion of the alcohol into the corresponding bromide was achieved using carbon tetrabromide and triphenylphosphine. Fully assigned 1H and 13C NMR spectra are presented and compared for all three compounds.

KW - 1H NMR

KW - 13C NMR

KW - COSY

KW - HSQC

KW - HMBC

U2 - 10.1016/j.molstruc.2025.141411

DO - 10.1016/j.molstruc.2025.141411

M3 - Article

SN - 0022-2860

VL - 1328

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 141411

ER -

Elucidation of some reactions of methyl 3-(benzyl(2-hydoxyethyl)amino)propionate using NMR

Abstract

Keywords

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