Hydrochloric Acid → 3-Amino-3-cyclopropylbutanamide

Participants

Reaction Steps

To a solution of 3-cyclopropyl-3-(1,1-dimethylethylsulfinamido)butanamide (442 mg, 1.79 mmol) in methanol (8 ml) was added a 4.0M solution of hydrochloric acid in dioxane (1.35 ml, 5.38 mmol) and the reaction mixture was stirred at room temperature for 1 h. Volatiles were removed in vacuo and the residue was dissolved in ethyl acetate. 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 ethyl acetate. The 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 gradient of dichloromethane/(solution of 3% aq. NH3 in methanol) to yield the title compound (213 mg, 83%); MS (ESI, m/z): 143.1 (M+H+).

Provenance & Evidence