Water → 1-Tert-butyl-4-(isocyanatomethyl)benzene

Participants

Reaction Conditions

Reaction Steps

4t-butylbenzylamine (3.2 g) was dissolved in dichloromethane (10 ml) and to the solution was added triethylamine (2.79 ml), followed by cooling to 0° C. and slowly adding dropwise a solution of triphosgene (1.98 g) in dichloromethane (5 ml). The mixture was stirred at room temperature for 5 hours and water (10 ml) was added thereto. The resulting mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by column-chromatography (hexane/ethyl acetate=20/1) to yield 4-t-butylbenzylisocyanate (880 mg) as a solid. The obtained compound (400 mg) and 3-fluorophenethylamine (290 mg) were dissolved in dichloromethane (20 ml) and the solution was stirred at room temperature for 22 hours. The solvent was removed therefrom and the residue was purified by column-chromatography (hexane/ethyl acetate=4/1) to yield the compound 29 (400 mg, 58%) as a solid.

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