Diisopropylamine → HCID 86743467, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 109 mg of 1,1-diethyl-3-(2-ethynyl-6-methyl-8α-ergolinyl)urea in 5 ml of absolute tetrahydrofuran is added dropwise at -30° C. to a solution of lithium diisopropylamide, prepared from 0.15 ml of diisopropylamine and 1.8 ml of 0.6-molar n-butyllithium solution (hexane) in 3 ml of absolute tetrahydrofuran at 0° C. within 15 minutes. After 30 minutes of agitation at -30° C., 0.07 ml of propyl iodide is added thereto. The mixture is stirred for one hour at -20° C. and overnight at room temperature. After evaporation, the mixture, after adding sodium bicarbonate solution and a small amount of ethanol, is extracted by shaking with ethyl acetate. The organic phase is concentrated and chromatographed over silica gel with toluene:glacial acetic acid:water=10:10:1, thus obtaining 30 mg of 1,1-diethyl-3-(2-ethynyl-1-propyl-6-methyl-8α-ergolinyl)urea as an oil.

Provenance & Evidence