(Diethylamino)sulfur trifluoride → HCID 59017206, compound

Participants

Reaction Steps

A solution of the material prepared in Example 25 (200 mg; 0.91 mmol) in dry ethyl acetate (10 ml) was cooled to −50° C. and (diethylamino)sulphur trifluoride (191 mg; 1.19 mmol) was added dropwise. The resultant solution was stirred at −50° C. for 1 h and then allowed to slowly warm to room temperature over a period of 3 h. The mixture was then poured onto a saturated aqueous NaHCO3 solution (50 ml) and further ethyl acetate (50 ml) added. After thorough mixing the organic layer was separated, washed sequentially with water (50 ml) and brine (50 ml), and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography to give the title compound as a pale yellow crystalline solid (60 mg). 1H NMR (CDCl3) δ 2.13 to 2.48 (m, 2H), 3.79 (qd, 1H), 4.09 (t, 1H), 4.25 to 4.35 (m, 2H), 4.43-4.49 (m, 1H), 5.333 (d, 1H), 7.04 (d, 1H) 7.15 (t, 1H), 7.41 (dd, 1H), 7.88 (dd, 1H); EIMS: m/z=222.2 [M+H]+

Provenance & Evidence