ChemInform Abstract: An Efficient Asymmetric Synthesis of (3S)‐3‐Amino‐1‐(4‐cyanophenyl)‐2‐oxopyrrolidine Hydrochloride Salt.

Abstract

AnEfficient Asymmetric Synthesis of (3S)-3-Amino-1-(4cyanophenyl)-2-oxopyrrolidine Hydrochloride Salt.-Coupling of bromide (II) with nitrile (III) and subsequent cyclization gives the lactam ring of the title compound. Displacement of the bromide in intermediate (IV) by treatment with excess NH 4 OH and work-up of the racemic amine with (R)-mandelic acid (V) leads to isolation of the racemic (R)-mandelic acid salt (VI). The optically pure title compound is then obtained through the dynamic resolution of amine (VI) in the presence of a catalytic amount of salicyl aldehyde and (R)-mandelic acid. -(COLSON, P.-J.; PRZYBYLA, C. A.; WISE, B. E.; BABIAK, K. A.; SEANEY, L. M.; KORTE, D. E.; Tetrahedron: Asymmetry 9 (1998) 15, 2587-2593; Monsato Life Sci., Searle, Synth. Dev., Skokie, IL 60077, USA; EN)