Sodium Iodide → tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate

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With cooling with ice, methanesulfonyl chloride (923 μl, 11.9 mmol) and triethylamine (1.94 ml, 13.9 mmol) were added to a dichloromethane (100 ml) solution of tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (2.00 g, 9.94 mmol), followed by stirring for 30 minutes with cooling with ice. The reaction liquid was concentrated under reduced pressure, dissolved in ethyl acetate, and washed with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was dissolved in acetone (50 ml), then sodium iodide (1.49 g, 9.94 mmol) was added, followed by heating under reflux in an oil bath at 85° C. for 5 hours. The reaction liquid was concentrated under reduced pressure, the residue was suspended in ethyl acetate, washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was dissolved in dimethylformamide (30 ml), then dimethylamine hydrochloride (2.43 g, 29.8 mmol) and potassium carbonate (2.75 g, 19.9 mmol) were added, followed by stirring at room temperature for 24 hours. The reaction liquid was concentrated under reduced pressure, the residue was suspended in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate and concentration, the resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (92.0 mg, 4%) as a colorless oily substance.

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