Convenient preparation of optically pure 3-aryloxy-pyrrolidines was written by Benard, Christophe;Mohammad, Rahim;Saraswat, Neerja;Shan, Rudong;Maiti, Samarendra N.;Wuts, Peter G. M.;Stier, Michael;Lints, Teresa;Bradow, James;Schwarz, Jacob B.. And the article was included in Synthetic Communications in 2008.Reference of 85838-94-4 This article mentions the following:
Chiral 3-methanesulfonyl-1-Boc-pyrrolidine and piperidine were reacted with sodium phenolates, resulting in a mixture of displacement and elimination products. Following carbamate deprotection and pH adjustment, the 3-pyrroline and tetrahydropyridine byproducts resulting from elimination were easily removed through aqueous partitioning and/or concentration Although the pyrrolidines were formed with a high degree of optical purity, slight racemization was observed for the piperidine case because elevated temperatures were required to effect displacement. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Reference of 85838-94-4).
tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Reference of 85838-94-4