99940-64-4Relevant articles and documents
Synthesis of Boc-protected 4,5-methano-β-proline
Tymtsunik, Andriy V.,Ivon, Yevhen M.,Komarov, Igor V.,Grygorenko, Oleksandr O.
, p. 3312 - 3315 (2014/06/09)
An efficient method for the preparation of Boc-protected 4,5-methano-β-proline - a novel bicyclic cyclopropane-containing β-amino acid - was developed, starting from readily available itaconic acid. A modified Simmons-Smith reaction was used for the construction of the cyclopropane ring. The method allowed for the synthesis of both cis and trans isomers of the title compound in 49% total yield and can be employed for gram-scale preparations. An approach to the preparation of methyl 5-oxopyrrolidine-3-carboxylate, which is one of the key intermediates in the synthetic scheme, on a multigram scale was also developed.
