Diisopropylethylamine → 1-ethyl-5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

Participants

Reaction Conditions

Reaction Steps

A mixture of (Z)-methyl N-3-methylbut-2-enoylpyrrolidine-1-carbimidothioate (1.19 g, 5.26 mmol, Eq: 1.00), ethylhydrazine oxalate (2.37 g, 15.8 mmol, Eq: 3) and N,N-diisopropyl ethyl amine (5.44 g, 7.15 ml, 42.1 mmol, Eq: 8) in dioxane (20 ml) was heated to 100° C., the resulting suspension was stirred for 3 hours at 100° C. The mixture was diluted with ethyl acetate and washed with water for 3 times. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 30-70% as eluent affording 1-ethyl-5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole (441 mg/38.1%) as a light yellow oil. MS: m/e=221.0 (M+H+)

Provenance & Evidence