Hydrogen Peroxide → HCID 66899040, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2-(4-bromophenyl)propan-2-yl)-6-((2-methyloxiran-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (57 mg, 128.4 μmol) in THF (10 mL) was added dropwise LiBEt3H (642 mL, 642 μmol) at 0° C. under nitrogen. The resulting mixture was stirred at 10° C. for 2 h. The reaction solution was cooled to 0° C. Hydrogen peroxide (10 mL) was added dropwise while maintain the temperature below 25° C. The resulting mixture was diluted with MTBE (50 mL), washed with water (50 mL) and 30 wt % aqueous sodium thiosulfate (50 mL×3). The organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative HPLC to afford 3-(2-(4-bromophenyl) propan-2-yl)-6-(2-hyroxy-2-ethylpropyl)-6-phenyl-1,3-oxazinan-2-one. 1H NMR: (CDCl3) δ 7.45-7.26 (m, 7H), 6.94-6.92 (d, 2H), 3.27-3.24 (m, 1H), 2.85-2.78 (m, 1H), 2.41-2.30 (m, 2H), 2.22 (m, 3H), 1.65 (s, 3H), 1.47 (s, 3H), 1.15 (s, 3H), 1.03 (s, 3H); LC-MS Method 2 tR=1.35 min, m/z=448, 446.

Provenance & Evidence