Codeine methyl ether → Thebaine

Participants

Reaction Steps

A solution of codeine methyl ether (343 mg, 1.00 mmol) in THF (10 ml, distilled from LiAlH4) was shaken vigorously with γ-MnO2 (440 mg, 5.0 mmol) under a nitrogen atmosphere at room temperature. Further portions of γ-MnO2 (440 mg, 5.0 mmol) were added at intervals of 1, 3, 5, and 10 hr. After 24 hr. the black mixture was filtered through a fine sintered glass funnel, the residue was washed with THF (4 × 50 ml), and the washings were combined with the original filtrate and evaporated to give 207 mg of crude thebaine. The MnO2 was then washed with methanol (4 × 30 ml) which yielded an additional 119 mg of crude thebaine. The two fractions were combined and crystallized from ethanol to give thebaine (251 mg, 80%) identical with an authentic sample by mp (191°-192°), TLC, GC, mass spectrum [m/e 311 (M+)] , and NMR.

Provenance & Evidence