(Trifluoromethyl)trimethylsilane → HCID 71152236, compound

Participants

Reaction Steps

To a solution of (3aR,5S,6S,7aR)-6-(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-5-carbaldehyde (0.650 g) in anhydrous THF (15 mL) at room temperature was TMSCF3 (0.750 mL, 5.08 mmol) followed by TBAF (1.0 M in THF, 0.10 mL, 0.10 mmol). The reaction was stirred at room temperature for 2 h. Another 2.50 mL of TBAF (1.0 M in THF) was added and the mixture was stirred at room temperature for 18 h. The solution was diluted with saturated aqueous NaHCO3 (30 mL), extracted with EtOAc (2×20 mL). The combined extract was dried over anhydrous Na2SO4. The solvents were evaporated under reduced pressure, and the residue was purified by silica gel column chromatography, eluted with 1%-3% 2 M NH3 MeOH solution in DCM to give 1-((3aR,5R,6S,7aR)-6-(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)-2,2,2-trifluoroethanol (0.274 g, 35%) as a pale yellow foam. MS m/z 391.1 (M+1, 100%). An estimation ratio of the two diastereomers was 70:30 based on its 1H NMR (400 MHz, CDCl3) spectrum.

Provenance & Evidence