Selective Hydrolysis of Ethyl 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate and Ethyl 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate as a Key Step in the Large-Scale Synthesis of Bicyclic Heteroaryl Carboxyaldehydes
Organic Process Research & Development2006Vol. 10(4), pp. 712–716
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Antonia A. Nikitenko, Michael W. Winkley, J. Zeldis, Kenneth A. M. Kremer, Alison Wah-on Chan, H. Strong, Mellard N. Jennings, Ivo Jirkovsky, Dieter Blum, Gulnaz Khafizova, G Grosu, Aradhana M. Venkatesan
Abstract
The isomeric mixture of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2- and −3-carboxylates (14 and 15), derived from a proline meso-ionic synthon, demonstrated remarkably different stabilities towards alkaline hydrolysis. On that basis, a nonchromatographic, highly efficient method for their large-scale separation was developed. The desired isomer 14 was converted into 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde, a key intermediate in the synthesis of bicyclic heteroaryl-substituted 6-alkylidene penems.
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