R. Galeazzi, G. Martelli, G. Mobbili
Oct 31, 2003
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The 4-benzyloxymethyl pyrrolidin-2-one, 5 , was alkylated leading to 3,4- trans -disubstituted pyrrolidin-2-one 6 in good yield and total diastereoselection, as shown by 1 H NMR data and NOE experiments. After reduction of the carbonyl group to give the trans -3,4-disubstituted pyrrolidine 7 , and removal of the chiral auxiliary, followed by protection of the nitrogen with t -Boc group, the corresponding N -protected pyrrolidine, 8 was obtained. The cleavage of the benzyl ether moiety, followed by oxidation of the hydroxy function, gave in good yield the corresponding pyrrolidine carboxylic acid 2 , a restricted analog of pregabalin.