Crystal Structure and Solution State Characterization of Lithium (S)-(1-(Bis(2-methoxyethyl)amino)-3-methylbutan-2-yl)(methyl)amide

Abstract

The solid state structure of lithiated (S)-N(1),N(1)-bis(2-methoxyethyl)-N(2),3-dimethylbutane-1,2-diamine, which is a chiral amide base synthesized from (S)-valine was determined by single-crystal X-ray diffraction. The complex in solution state is also characterized by a variety of NMR experiments including diffusion-ordered NMR spectroscopy (DOSY) with diffusion coefficient-formula weight correlation analyses and other one- and two-dimensional NMR techniques by dissolving the crystal in toluene-d8. The crystallography and NMR results suggest that the chiral amide is dimeric in both solid and solution states.