Addition of methylmagnesium iodide to 3,3,5,5-tetramethylcyclohexanone (I) produced the tertiary alcohol (II). Subsequent treatment of alcohol (II) with hydrazoic acid in the presence of TiCl4 gave azide (III). This was then reduced with LiAlH4 to the corresponding amine, which was isolated as the hydrochloride salt.
In an alternative method, the Ritter reaction of alcohol (II) with chloroacetonitrile in the presence of H2SO4 yielded the chloroacetamide (IV). This was then hydrolyzed to the desired amine by treatment with thiourea in HOAc-EtOH.