Lithium tri-s-butylborohydride → HCID 58746935, compound

Participants

Reaction Steps

A solution of tert-butyl [(1S)-2-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate (70 mg, 92.1 μmol) and tetrahydrofuran (20 mL) was stirred at −78° C. After stirring for 5 min, 1.0 M L-selectride in tetrahydrofuran (92 μL) was added dropwise. The reaction was quenched with glacial acetic acid (0.7 mL). The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (65 mg, 83%). MF=C35H49BrN4O6SSi; LCMS found for C35H50BrN4O6SSi(M+H)+: m/z=761.

Provenance & Evidence