Codeine methyl ether → Thebaine

HRID 442333

Reaktionsgleichung

Reaktionsgleichung von HRID 442333
[CH3:1][N:2]1[C@@H:7]2[CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]4[O:17][C@H:18]5[C@@H:19]([O:22][CH3:23])[CH:20]=[CH:21][C@@H:6]2[C@:5]5([C:10]=34)[CH2:4][CH2:3]1>C1COCC1>[CH3:1][N:2]1[C@@H:7]2[CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]4[O:17][C@H:18]5[C:19]([O:22][CH3:23])=[CH:20][CH:21]=[C:6]2[C@:5]5([C:10]=34)[CH2:4][CH2:3]1

Komponenten

3

Edukt 1

HCID 5492619Codeine methyl ether

Produkt 1

HCID 5324289ThebaineAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationthe black mixture was filtered through a fine sintered glass funnel
  2. washthe residue was washed with THF (4 × 50 ml)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-957de762f68d4b00b84dcd4786660672
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04045440

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