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

Reaction equation

[CH:1]1([CH2:4][C:5]([NH:13]S(C(C)(C)C)=O)([CH3:12])[C:6]2[O:7][C:8]([CH3:11])=[N:9][N:10]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>CO>[CH:1]1([CH2:4][C:5]([C:6]2[O:7][C:8]([CH3:11])=[N:9][N:10]=2)([NH2:13])[CH3:12])[CH2:3][CH2:2]1

Participants

Procedure

To a solution of N-[2-cyclopropyl-1-methyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]-2-methyl-propane-2-sulfinamide (example 173a, 520 mg, 1.46 mmol) in MeOH (8 ml) was added a 4M solution of hydrochloric acid in dioxane (729 μl, 2.92 mmol). The reaction mixture was stirred at room temperature for 1 hour. Reaction was quenched by addition of potassium carbonate and stirred for 15 minutes. The insolubles were removed by filtration and the filtrate was 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 (130 mg, 50%). MS (ESI, m/z): 182.2 (M+H+).