Ethyl Acetate → HCID 18512114, compound

Participants

Reaction Steps

The product from Example 19B (2.93 g, 6.72 mmoles ) and 4-methyl-morpholine N-oxide (0.8660 g, 7.4 mmoles) in acetone (30 mL) and water (4.3 mL) were treated with osmium tetroxide (1.7 mL, 0.0168 mmoles, 2.5 wt % solution in 2-methyl-2-propanol) and allowed to stirr at room temperature overnight. The mixture was then treated with 1,4-Diazabicyclo[2.2.2]octane (0.05 g) and 4-methyl-morpholine N-oxide (0.8660 g, 7.4 mmoles) and allowed to stir for an additional 24 hours. Saturated NaHSO3 (250 mL) and ethyl acetate (250 mL) were added and the reaction mixture was stirred vigorously for 2.5 hours. The mixture was partitioned and the organic phase washed with brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, ethyl acetate) to provide the title compound as a yellow oil (3.0 g, 95%).

Provenance & Evidence