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A Solid-state NMR Study of Formoterol Fumarate

Markwell, Andrew Fraser (2009) A Solid-state NMR Study of Formoterol Fumarate. Masters thesis, Durham University.



Spectra have been obtained for each of the three formoterol fumarate solvates diethanol, diisopropanol and dibenzyl alcohol and, with the aid of solution-state data and dipolar dephasing experiments, carbon-13 spectral assignments have been made. It was shown that diethanol and diisopropanol solvates are relatively stable to magic-angle spinning but do gradually convert to anhydrate C. The coalescence temperature of the methoxybenzene carbon atoms for diethanol, diisopropanol solvates and anhydrate C were found and an exchange rate for this ring-flip calculated. The formoterol fumarate dihydrate, anhydrate A, anhydrate B and anhydrate C have been prepared and spectra obtained, again with the aid of solution-state data and dipolar dephasing experiments carbon-13 spectral assignments have been made where possible. (^13)C and (^2)H T(_1) measurements suggest that the fumarate ion is mobile in the anhydrate C structure. A (^2)H DPMAS spectrum, however does not indicate isotropic motion for the ion. Water measurements of anhydrate A and anhydrate C indicate them to contain water. It is believed that this water is hydrogen bonded to the NH(_2)+ ion and is difficult to remove by heating. A route for preparing the solvates by bypassing the need to dry the dihydrate has-been found. An ethyl acetate solvate of formoterol fumarate was produced by slurrying anhydrate C with ethyl acetate.

Item Type:Thesis (Masters)
Award:Master of Science
Thesis Date:2009
Copyright:Copyright of this thesis is held by the author
Deposited On:08 Sep 2011 18:25

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