Acetic Acid → Hydromorphone

Participants

Reaction Conditions

Reaction Steps

A 100 mL Schlenk tube was charged with methanol (50 mL), morphine free base (5.0 g, 17.52 mmol) and sodium methoxide (47.4 mg, 0.876 mmol). The mixture was stirred and heated to reflux under nitrogen for 15 min then treated with the solution of the catalyst added by a pipette. The resulting brown solution was stirred and heated to reflux under nitrogen for 1 hour, cooled to 7° C. in an ice bath, treated with acetic acid (0.05 mL, 0.876 mmol), stirred for another 30 min and filtered. The filtered solid was washed with isopropanol (3×8 mL) and dried in an oven at 95° C. to give hydromorphone free base as a white solid. The yield was 4.12 g, 82.4%.

Provenance & Evidence