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Into a 500-mL round-bottom flask, was placed a solution of 2-(methoxymethyl)-4-methyl-4,5-dihydro-1H-imidazole (compound 222.1, 19 g, 148.4 mmol) in acetonitrile (200 mL). Al2O3 (19 g, 182.7 mmol) was added to the reaction. This was followed by the addition of potassium permanganate (58 g, 367.1 mmol) in several batches at 0° C. The reaction mixture was stirred for 2 h at 0° C., then warmed to room temperature overnight. The reaction was quenched with 20 mL of sodium sulfite (sat.). The solids were removed by filtration and the filtrate was concentrated under reduced pressure. This resulted in 19 g (crude) of the title compound as yellow oil.

1. customInto a 500-mL round-bottom flask, was placed
2. temperaturewarmed to room temperature overnight
3. customThe reaction was quenched with 20 mL of sodium sulfite (sat.)
4. customThe solids were removed by filtration
5. concentrationthe filtrate was concentrated under reduced pressure