Triethylamine → tert-Butyl [3-(cyclopropylamino)propyl]methylcarbamate

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Reaction Steps

The compound (300 mg, 1.59 mmol) obtained in Example 25b was dissolved in ethyl acetate (16 mL), triethylamine (0.323 mL, 2.39 mmol) and methanesulfonyl chloride (0.147 mL, 1.90 mmol) were added under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. Insoluble matter was removed by filtration through celite, the solvent was evaporated under reduced pressure, the resulting residue was added dropwise to a solution of cyclopropylamine (1.82 g, 31.8 mmol) in methanol (3 mL) under ice cooling, and the mixture was stirred at 60° C. for 72 hours. The solvent was evaporated under reduced pressure, 1 N sodium hydroxide was added to the resulting residue, and the mixture was extracted with ethyl acetate (×3). The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1→10:1, v/v) to give the title compound (215 mg; yield, 59%) as a yellow oily substance.

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