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Synthesis of methyl (±)-3,5-bis(substitutedmethyl)pyrrolidine-2-carboxylates: a convenient approach to proline-mimetics |
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| Authors: | Joana Ferreira da Costa,Franco Ferná ndez,Xerardo Garcí a-Mera,Pilar Midó n |
| Affiliation: | a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, E-15782, Santiago de Compostela, Spain b Instituto de Farmacia Industrial, Facultade de Farmacia, Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain c CIQ- Departamento de Química, Facultade de Ciencias, Universidade de Porto, Rua do Campo Alegre, 687, 4169-007, Porto, Portugal |
| Abstract: | Starting from readily available N-benzyl protected methyl 3,5-bis(hydroxymethyl)pirrolidinecarboxylate a number of racemic methyl t-3,t-5-disubstitutedprolinates have been synthesised, thus opening a practical way towards the preparation of a variety of putative proline-mimetics. In this context, N-Boc protected derivatives proved to be better intermediates than their N-benzyl counterparts in terms of cleanness and overall yield of the synthetic procedure. |
| Keywords: | Synthesis Pyrrolidine-2-carboxylates Proline-mimetics Peptides |
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