(Trifluoromethyl)trimethylsilane → HCID 123531119, compound

Participants

Reaction Steps

To a solution of tert-butyl ((3aR,5S,6R,7S,7aR)-6-(benzyloxy)-7-fluoro-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.352 g, 0.829 mmol) and TMSCF3 (0.290 g, 2.04 mmol) in anhydrous THF (15 mL) was added TBAF (1.0 M in THF, 0.050 mL, 0.050 mmol). After addition the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was cooled at 0° C., and another batch of TBAF (1.0 M in THF, 1.5 mL, 1.5 mmol) was added. The mixture was stirred at room temperature for another 2 h, and then diluted with EtOAc (20 mL) and brine (50 mL). The organic layer was collected, and the aqueous was extracted with EtOAc (20 mL). The combined extract was dried over anhydrous Na2SO4. After filtration the solvent was evaporated under reduced pressure, and the residue was purified and separated on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:10 to 2:3), affording tert-butyl ((3aR,5R,6R,7S,7aR)-6-(benzyloxy)-7-fluoro-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate as a pale yellow solid (0.141 g, 34%). 1H NMR (400 MHz, CDCl3) δ 7.37-7.28 (m, 5H), 6.14 (d, J=7.5 Hz, 1H), 5.09 (td, J=4.1, 46.4 Hz, 1H), 4.87 (d, J=10.8 Hz, 1H), 4.38-4.30 (m, 1H), 4.50 (d, J=10.8 Hz, 1H), 4.25-4.22 (m, 1H), 4.10-4.06 (m, 2H), 3.27 (s, 3H), 1.52 (s, 9H).

Provenance & Evidence