(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one → Oxycodone

Participants

Reaction Steps

To the solution of 14-hydroxycodeinone produced in Example 14 is added 0.5 g of 5% palladium on carbon, 50% wet. The mixture is hydrogenated at 30 to 40 psi for a period of 18 to 25 hours at ambient temperature. The catalyst is filtered off and is washed with 5 ml of water. The filtrate is cooled to 0–5° C. and with stirring, sufficient concentrated (28–30%) ammonium hydroxide is added to raise the pH to 10–12. The resulting suspension is stirred at 0–5° C. for 1–2 hours. The solid is filtered off and is washed with two 5 ml portions of water. The product is dried in vacuo (e.g., 50 mm Hg) at 30–40° C. to yield 8.1 g of oxycodone (85% yield based on thebaine bitartrate). The product purity is better than 98%.

Provenance & Evidence