Reaktion #82145

ord-0aa465a90faf45259833d00a44a98cf2

Reaktionsgleichung

CCOCC
ether
CC(=O)OC(C)=O
acetic anhydride
CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5
morphine
→
CC(=O)C1(O)CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@]45CCN3C
3-acetylmorphine
Ausbeute 80.0%

Edukte

CCOCC
ether
CC(=O)OC(C)=O
acetic anhydride
CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5
morphine
—
ice

Reagenzien

Keine

Lösungsmittel

O=C([O-])O.[Na+]
sodium bicarbonate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    Extraktionthe solution was extracted with dichloromethane (200 ml)
  3. 3
    ExtraktionThe organic extract
  4. 4
    Waschenwas washed with brine
  5. 5
    Trocknendried over Na2SO4
  6. 6
    Sonstigethe solvent removed in vacuo
  7. 7
    Sonstigeto leave a sticky white residue

Vorschrift

To a stirred suspension of morphine (4 g, 14 mmol) in 10% aqueous sodium bicarbonate (377 ml) was added acetic anhydride (19 ml) over 8.5 minutes. 15 minutes after the addition, ice cold water (300 ml) was added and the solution was extracted with dichloromethane (200 ml). The organic extract was washed with brine, dried over Na2SO4, and the solvent removed in vacuo to leave a sticky white residue. Trituration with ether gave 3-acetylmorphine (3.68 g, 80%). The corresponding 3-pivalyl, 3-isobutyryl, 3-propionyl and other 3-acyl derivatives of morphine were also prepared.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05621087uspto-grants-1997_04