Reaktion #2360066

ord-b69d4aead2744f77805804183feba95f

Reaktionsgleichung

CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
Oxymorphone
→
CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
Oxymorphone
CN1CCC23c4c5ccc(O)c4OC2C(O)CCC3(O)C1C5
6α-oxymorphol
CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@H](O)CC[C@@]3(O)[C@H]1C5
6β-oxymorphol

Edukte

CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
Oxymorphone

Reagenzien

Keine

Lösungsmittel

CCCO
1-propanol

Reaktionsbedingungen

Temperatur
90°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas charged
  2. 2
    Sonstigewas lowered to 25±5° C.
  3. 3
    workup.STIRRINGstirred for 1 h
  4. 4
    TemperaturThe batch was further cooled to 10±5° C.
  5. 5
    workup.STIRRINGstirred 1 h
  6. 6
    FiltrationThe product was collected by filtration
  7. 7
    Waschenwashing the cake with 1-propanol (10±5° C., 2×48.2 g)
  8. 8
    Sonstigethen drying under vacuum at 55±5° C.

Vorschrift

The crude Oxymorphone Base (267.7 g wet, 180.1 g dry basis) was transferred back to a clean 3000 mL reaction vessel and 1-propanol (321.6 g) was charged. The slurry was heated to 90±3° C. and stirred for 1.5 h. The temperature was lowered to 25±5° C. and stirred for 1 h. The batch was further cooled to 10±5° C. and stirred 1 h. The product was collected by filtration washing the cake with 1-propanol (10±5° C., 2×48.2 g) then drying under vacuum at 55±5° C. to give Oxymorphone Base (167.8 g, 83.3% yield, 99.9 area %, 6α-oxymorphol 0.11 area %, 6β-oxymorphol not detected).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120800B2uspto-grants-2015_09