Triethylsilane → HCID 86706974, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylsilyl trifluoromethanesulfonate (2.9 g, 13 mmol) and triethylsilane (2.6 g, 22 mmol) were added to a solution of 4-benzyl-2-(3-methyl-1,2-oxazol-5-yl)morpholin-2-ol (C36) (1.2 g, 4.4 mmol) in dichloromethane (15 mL), and the reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was then adjusted to a pH of 5 to 6 via addition of saturated aqueous sodium bicarbonate solution. After extraction with dichloromethane (3×20 mL), the combined organic layers were washed with saturated aqueous sodium chloride solution (25 mL), dried over sodium sulfate, filtered, and concentrated. Purification via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in petroleum ether) afforded the product as a yellow oil. Yield: 500 mg, 1.9 mmol, 43%. LCMS m/z 258.9 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 7.27-7.37 (m, 5H), 6.07 (s, 1H), 4.75 (dd, J=9.7, 2.3 Hz, 1H), 3.96 (ddd, J=11.3, 2.8, 2.4 Hz, 1H), 3.81 (ddd, J=11.3, 10.8, 2.5 Hz, 1H), 3.52-3.61 (m, 2H), 3.02 (br d, J=11.4 Hz, 1H), 2.68-2.75 (m, 1H), 2.29 (s, 3H), 2.27-2.37 (m, 2H).

Provenance & Evidence