Ammonia → (RS)-3-allyl-3-cyclopenten-1-yl 2,2,3,3-tetramethylcyclopropanecarboxylate

Participants

Reaction Steps

To a mixture of (RS)-3-allyl-3-cyclopenten-1-ol (300 mg), 2,2,3,3-tetramethylcyclopropanecarboxylic acid (343 mg), 4-dimethylaminopyridine (5 mg), triethylamine (733 mg) and dichloromethane (10 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was added under ice-cooling. The resulting reaction mixture was further allowed to react for 8 hours at room temperature. Then aqueous ammonia (10 ml) was added to the reaction mixture and the reaction mixture was stirred vigorously for 2 hours. The reaction solution was extracted twice with diethyl ether. After the combined ether layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to afford 45 mg of (RS)-3-allyl-3-cyclopenten-1-yl 2,2,3,3-tetramethylcyclopropanecarboxylate (Compound No. 117). Yield 8%

Provenance & Evidence