Methyl morpholine oxide → HCID 66634692, compound

Participants

Reaction Steps

(11S,15S)-16-Methylidene-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one obtained in Example 1 (0.730 g, 1.22 mmol) and N-methyl morpholine oxide (50 wt-% solution in water, 1.25. mL, 5.34 mmol) were suspended in dichloromethane (60 mL). Osmium tetroxide (4 wt-% solution in water, 0.37 mL, 0.060 mmol) was added to the suspension. The mixture was stirred vigorously at rt. After most of starting material had been consumed (over week-end), NalO4 (0.52 g, 2.44 mmol) was added and the reaction was stirred for an additional 30 min. The reaction was quenched by addition of aqueous sodium thiosulfate (50 mL) and the phases were separated. The aqueous phase was extracted with dichloromethane (2×50 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give 630 mg (85% yield) of the product in 75% purity. Another batch of ketone has been purified by filtration through a pad of silica topped with celite and eluting with Heptane:EtOAc 1:1. LCMS: ACE 3 C8, 50×3.0 mm, 10% to 97% acetonitrile in 0.1% TFA in water, 1 mL/min; Rt=2.091.

Provenance & Evidence