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 tert-butyl tert-butoxycarbonyl(4-((3R,4R,5S)-3-((tert-butoxycarbonyl)amino)-4-((tert-butyldimethylsilyl)oxy)-5-methylpiperidin-1-yl)pyridin-3-yl)carbamate (1.0 equiv.) in THF (0.20 M) at RT was added TBAF (1.0 equiv.). The resulting mixture was stirred at rt for 4 hrs. The reaction mixture was then diluted with EtOAc and water. The organic layer was washed with Brine, dried over MgSO4, concentrated and purified by flash column chromatography to yield tert-butyl tert-butoxycarbonyl(4-((3R,4R,5S)-3-((tert-butoxycarbonyl)amino)-4-hydroxy-5-methylpiperidin-1-yl)pyridin-3-yl)carbamate in 87% yield. LC/MS (m/z)=523.4 (MH+), Rt=0.72 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 1.03 (d, J=6.65 Hz, 3 H), 1.34-1.51 (m, 54 H), 1.72-1.87 (m, 1 H), 2.05 (s, 1 H), 2.46-2.57 (m, 1 H), 2.69 (t, J=11.35 Hz, 1H), 2.78-2.94 (m, 1 H), 3.00-3.14 (m, 1 H), 3.45 (d, J=12.52 Hz, 1 H), 3.53-3.76 (m, 1H), 4.63 (d, J=6.26 Hz, 1 H), 6.88 (d, J=5.48 Hz, 3 H), 8.13 (s, 3 H), 8.26-8.36 (m, 3 H).

Provenance & Evidence