m-Chloroperbenzoic acid → 14-Hydroxymorphinone

Participants

Reaction Steps

According to literature methods for the preparation of oxycodeinone from thebaine,[16] oripavine (1.00 g of 78% w/w, 2.62 mmol) was treated with two portions of m-CPBA (0.82 g in total of max 77% reagent, approx. 3.66 mmol) in HOAc (4.5 mL) and TFA (0.35 mL). When the reaction was complete, the mixture was poured into ice-water (20 mL). After stirring for 30 min, the solid was removed by filtration. The filtrate was extracted with CHCl3 (5 mL×2), made basic to pH 9 with conc. NH4OH, and extracted with CHCl3/i-PrOH (5:1; 20 mL×4). The latter extracts were combined, dried (Na2SO4), filtered and concentrated to give oxymorphinone (B1) as an off-white solid, 670 mg (85%).

Provenance & Evidence