Synthesis, hydrolysis, and reductive cyclization of ethyl 5-chloro-4-(4-nitropyrrolidin-3-yl)pyrrole-3-carboxylates

Ethyl 5-chloro-4-(2-nitroethenyl)pyrrole-3-carboxylates, obtained by the condensation of ethyl 5-chloro-4-formylpyrrole-3-carboxylates with nitromethane, react with N-methylazomethine ylide with the formation of ethyl 5-chloro-4-(4-nitropyrrolidin-3-yl)pyrrole3-carboxylates. Their hydrolysis yielded the corresponding acids, while reductive cyclization led to the synthesis of hexahydrodipyrrolo[3,4-b:3',4'-d]pyridin-5(1H)-one via intermediate ethyl 4-(4-aminopyrrolidin-3-yl)-5-chloropyrrole-3-carboxylate derivatives.

Automated summary

Ethyl 5-chloro-4-(2-nitroethenyl)pyrrole-3-carboxylates were synthesized from the condensation of ethyl 5-chloro-4-formylpyrrole-3-carboxylates with nitromethane. These compounds reacted with N-methylazomethine ylide to form ethyl 5-chloro-4-(4-nitropyrrolidin-3-yl)pyrrole-3-carboxylates. Hydrolysis and reductive cyclization of these compounds led to the synthesis of hexahydrodipyrrolo[3,4-b:3',4'-d]pyridin-5(1H)-one via intermediate ethyl 4-(4-aminopyrrolidin-3-yl)-5-chloropyrrole-3-carboxylate derivatives.