HCID 45086957, compound → HCID 58997949, compound

Participants

Reaction Steps

Scandium triflate (730 mg, 1.48 mmol) was added to a stirred suspension of (2R,3S)—N-(2-hydroxyphenyl)-3-phenyloxirane-2-carboxamide (64b) in dry acetonitrile (150 mL) under nitrogen. The mixture was stirred at ambient temperature for 24 hours then heated at reflux for an additional 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate, and filtered through diatomaceous earth. Evaporation afforded an off-white solid which was purified by flash chromatography on silica gel eluting with 10:1 (v/v) dichloromethane: ethyl acetate to afford the title compound (2.290 g, 60%) as a white solid. TLC Rf=0.20 (10:1 dichloromethane:ethyl acetate). 1H NMR (300 MHz, CDCl3) δ3.70 (d, 1H, J=5 Hz), 4.63 (m, 1H), 5.28 (d, 1H, J=10 Hz), 6.89 (m, 1H), 7.02-7.16 (m, 3H), 7.35-7.47 (m, 5H), 7.78 (br, 1H). MS APCI, m/z=256 (M+1). LC/MS: 1.84 min. [α]D 25=+288° (c=5.0, CHCl3).

Provenance & Evidence