Synthesis and Crystal Structure of (2S,2'S,4'R)-2-(1-Hydroxy-1-ethylpropyl)-1-[(1'-p-tosyl-4'-hydroxypyrrolidin-2'-yl)methyl]pyrrolidine

1 INTRODUCTION In recent years, chiral β-amino alcohols have attracted much attention due to their special bio- logical functions and catalytic activities. Chiral β- amino alcohol moieties are usually found not only in natural products (e.g., cinchona alkaloids, ephe- drine, toxal, etc.) with special biological activities1, 2], but also critical structural segments of some syn- thesized biologically active compounds, such as adrenergic agonists or antagolist3, 4] and inhibitors for HI…

Synthesis and Crystal Structure of (2S,2 'S,4 'R)- 2-(1-Hydroxy- 1-ethylpropyl)- 1-[ (1'-p-tosyl-4 '-hydroxypyrrolidin-2'-yl)methyl]pyrrolidine

The title compound (2S,2'S,4'R)-2-(1hydroxy- 1 -ethylpropyl)- 1 -(1'-p-tosyl-4'-hydroxypyrolidin-2'-yl)methyl]pyrrolidine synthesized by using (2S,4R)-4-hydroxy-L-proline and L-proline as the main materials was characterized through IR, 1H NMR, 13C NMR and HRMS spectra as well as single-crystal X-ray diffraction analysis. There is one equivalent ethanol involved in the crystal (C23H40N2O5S, Mr = 456.63). The crystal belongs to the triclinic system, space group P1, a = 6.5628(13), b = 8.4228(17), c = 11.957(2) (A), α = 80.54(3),β = 83.19(3), γ = 89.89(3)°, V=647.3(2) (A)3, Z = l, Dc = 1.171 g/cm3, λ(MoKα) = 0.71073 (A),μ = 0.158 mm-1, F(000) = 248, the final R = 0.0465 and wR = 0.1336 for 1769 observed reflections with I ＞ 2σ(I). The adjacent molecules of compound 5 are linked through intermolecular hydrogen bonds formed by the secondary hydroxy group of one molecule with the tertiary hydroxy group of another one, and the molecular chains are further linked by ethanol through two kinds of hydrogen bonds with two molecules from different chains respectively to form a supramolecular structure.