Triethylamine → (RS)-1-(2-azido-propyl)-6-chloro-1,4-dihydro-indeno[1,2-b]pyrrole

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Reaction Steps

1.2 ml of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 1.9 g of (RS)-1-(6-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 4.3 ml of triethyl-amine in 60 ml of dichloromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 150 ml of dichloromethane, washed twice with 70 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 70 ml of dichloromethane. The combined organic phases were washed with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 40 ml of anhydrous dimethylformamide, treated with 1.0 g of sodium azide and the reaction mixture was heated to 50° for 17 hours while stirring. After cooling, the solution was poured into 140 ml of water and extracted twice with 140 ml of diethyl ether each time and once with 140 ml of ethyl acetate. The combined organic phases were washed once with 140 ml of water and once with 140 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (toluene). 0.8 g (38%) of (RS)-1-(2-azido-propyl)-6-chloro-1,4-dihydro-indeno[1,2-b]pyrrole was obtained as a yellowish oil.

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