1-{[4-Ethoxymethoxy-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester → 17-Ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]-octadec-7-ene-4-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

The diene (1d) (1.75 g) was dissolved in dry dichloroethane (800 ml, 0.0046M solution). The solution was bubbled with argon for 10 min whereafter Hoveyda-Grubbs 1:st gen. catalyst (20 mg 3.5 mol %) was added and the reaction mixture was stirred at 95° C. overnight. Additional catalyst (25 mg) was added to the reaction mixture (at argon flow) and the reaction was stirred at 97° C. The reaction mixture was cooled to room temperature and scavenger (100 mg) was added and reaction mixture was stirred for 4 h at room temperature. The reaction mixture was filtered, the filtrate was concentrated by rotary evaporation and the residue was purified by column chromatography on silica which gave the pure title compound (1.23 g. Yield 75%).

Provenance & Evidence