Potassium Carbonate → tert-Butyl 3-[5-acetyl-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate

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Reaction Steps

Potassium carbonate (15.0 g, 108 mmol) was added to a solution of 1-fluoro-4-{isocyano[(4-methylphenyl)sulfonyl]methyl}benzene (C2, see Organic Syntheses; Wiley & Sons: New York, 2004; Collect. Vol. 10, p. 692) (12.5 g, 43.2 mmol) and tert-butyl 3-{[(1E)-2-oxopropylidene]amino}azetidine-1-carboxylate (C1) (10 g, 44 mmol) in DMF (150 mL). The mixture was stirred for 16 hours at room temperature, then partitioned between ethyl acetate (500 mL) and water (500 mL). The organic layer was washed with water (3×500 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Eluant: 1:1 petroleum ether: ethyl acetate) to give the product as a solid. Yield: 11 g, 31 mmol, 72%.

Provenance & Evidence