Tetrabutylammonium Fluoride → tert-butyl tert-butoxycarbonyl(4-((3R,4R,5S)-3-((tert-butoxycarbonyl)amino)-4-hydroxy-5-methylpiperidin-1-yl)pyridin-3-yl)carbamate

Participants

Reaction Steps

To a solution of di-tert-butyl [4-((3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methylpiperidin-1-yl)pyridin-3-yl]imidodicarbonate (1.01 g, 1.58 mmol) in THF (7.9 mL) at room temperature 1.0 M tetra-n-butylammonium fluoride in THF (1.66 mL, 1.66 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. The mixture was then diluted with EtOAc and water and the layers were separated. The organic layer was washed with brine, dried, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using CombiFlash® apparatus (0 to 80% EtOAc in hexanes) to give the sub-title compound (771 mg, 93%). LCMS calc. for C26H43N4O7 (M+H)+: m/z=523.3. Found: 523.2.

Provenance & Evidence