Citric Acid → Ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-4-nitrobutanoate

Participants

Reaction Steps

A 9.46 g (25.3 mmol) portion of ethyl (E)-3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]acrylate was dissolved in 50 ml of nitromethane to which, while cooling in an ice bath and stirring, was subsequently added dropwise 3.78 ml (25.3 mmol) of diazabicycloundecene. After 10 minutes of stirring, the reaction mixture was further stirred at room temperature for 1 hour. While cooling in an ice bath and stirring, the reaction solution was acidified by gradually adding 10% citric acid aqueous solution and then mixed with ethyl acetate to effect separation of layers. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under a reduced pressure to give 11.45 g (25.26 mmol) of the title compound. The thus obtained compound was used in the following reaction without purification.

Provenance & Evidence