Triethylamine → (RS)-1-(2-azido-propyl)-7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrole

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Reaction Steps

0.81 ml of methanesulfonyl chloride was added dropwise while is stirring to a solution, cooled to 0°, of 1.35 g of (RS)-1-(7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 2.9 ml of triethylamine in 40 ml of dichloromethane. The reaction mixture was subsequently added to 70 ml of water, extracted twice with 100 ml of dichloromethane each time and the combined organic phases were washed once with 70 ml of saturated sodium hydrogen carbonate solution and once 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 0.68 g of sodium azide and the reaction mixture was heated to 80° while stirring for 23 hours. After cooling the solution was poured into 70 ml of water and extracted twice with 100 ml of ethyl acetate each time. The combined organic phases were washed once with 70 ml of water and once with 70 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). 0.93 g (62%) of (RS)-1-(2-azido-propyl)-7-methoxy-2-methyl-1,4-dihydro-indeno[1,2-b]pyrrole was obtained as a colorless oil.

Provenance & Evidence