1,1,1,3,3,3-Hexafluoro-2-propanol → (2S,3R,4R,5S)-2,5-bis(4-(benzyloxy)phenyl)-1-(4-tert-butylphenyl)pyrrolidine-3,4-diol

Participants

Reaction Steps

To a solution of (1R,1′R)-1,1′-((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)diethane-1,2-diol (200 mg, 0.90 mmol) in methanol (6 ml) and dichloromethane (3 ml) was added iodobenzene diacetate (696 mg, 2.16 mmol) and the solution was stirred at room temperature for 5 h. Solution was concentrated and to the residue was added 0.1M H2SO4 (4 ml) and stirring was continued at room temperature for 18 h. The pH was adjusted to ˜6 with solid NaHCO3, and 4-tert-butylaniline (287 μl, 1.80 mmol) was added followed by 4-benzyloxyphenylboronic acid (369 mg, 1.62 mmol) and hexafluoroisopropyl alcohol (4 ml) and stirred at 60° C. for 2 h. Solvent was concentrated and the residue dissolved in ethyl acetate, washed with H2O, 0.33M K3PO4, brine, dried (Na2SO4), filtered and concentrated to give crude product which was purified by chromatography on silica gel eluting with 0-20% ethyl acetate/dichloromethane to give title compound (249 mg, 46%).

Provenance & Evidence