Synthesis, crystal structure and DFT study of 1,1-dimethylethyl (2R)-2-(hydroxydiphenylmethyl)-1-pyrrolidinecarboxylate

Abstract

During the asymmetric reduction process of Corey Bakshi Shibata chiral reagent, the target compound 1,1-dimethylethyl (2R)-2-(hydroxydiphenylmethyl)-1-pyrrolidine carboxylate was unexpectedly discovered. The structure was characterized by 1H NMR, 13C NMR, MS, and FT-IR. The crystal belongs to orthogonal crystal system, space group P212121, crystal cell parameters: a = 8.9941(8) Å, b = 9.8001(9) Å, c = 22.706(2) Å, α = 90°, β = 90°, γ = 90°, μ (MoKα) = 0.71073 Å mm−1. DFT further analyzed its structure. The frontier molecular orbital and molecular electrostatic potential of the target compound were further studied.