Sodium Chloride → HCID 86749894, compound

Participants

Reaction Steps

0.29 ml (3.79 mmol) of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 0.49 g (1.9 mmol) of (R)-1-(7-ethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-1-yl)-propan-2-ol and 1.06 ml (7.6 mmol) of triethylamine in 30 ml of dichloromethane and the mixture was stirred at this temperature for a further 50 minutes. The reaction mixture was subsequently diluted with 100 ml of dichloromethane, washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 50 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 yellowish solid obtained was dissolved in 25 ml of anhydrous dimethylformamide, treated with 0.25 g (3.8 mmol) of sodium azide and the reaction mixture was heated to 70° while stirring for 22 hours. After cooling, the solution was poured into 70 ml of semi-saturated sodium chloride solution and extracted twice with 70 mi of diethyl ether each time. The combined organic phases were washed once with 50 ml of water and once with 50 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 (ethyl acetate). 0.53 g (99%) of (S)-1-(2-azido-propyl)-7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazole was obtained as a light yellow solid.

Provenance & Evidence