Hydrochloric Acid → 2,2-Dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propan-1-amine

To a solution of N-[2,2-dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propyl]-2-methyl-propane-2-sulfinamide (example 174a, 462 mg, 1.69 mmol) in methanol (10 ml) was added a 4M solution of hydrochloric acid in dioxane (845 μl, 3.38 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was then concentrated in vacuo and the residue was dissolved in ethylacetate. The organic phase was extracted with a 2M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. Combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (165 mg, 58%). MS (ESI, m/z): 170.5 (M+H+).