Oxymorphone → HCID 627484, compound

HRID 2272884Notes

Reaction equation

HRID 2272884 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15]>C(O)CC>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15].[CH3:1][N:2]1[CH:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([OH:22])=[C:11]4[O:12][CH:13]5[CH:14]([OH:15])[CH2:16][CH2:17][C:18]2([OH:21])[C:5]5([C:6]=34)[CH2:4][CH2:3]1.[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([OH:22])=[C:11]4[O:12][C@H:13]5[C@H:14]([OH:15])[CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 5284604Oxymorphone

Product 3

HCID 627484HCID 627484, compoundHCID 5284604OxymorphoneHCID 21779240beta-Oxymorphol

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  1. additionwas charged
  2. customwas lowered to 25±5° C.
  3. stirringstirred for 1 h
  4. temperatureThe batch was further cooled to 10±5° C.
  5. stirringstirred 1 h
  6. filtrationThe product was collected by filtration
  7. washwashing the cake with 1-propanol (10±5° C., 2×48.2 g)
  8. customthen drying under vacuum at 55±5° C.

Sources & evidence

ORD record
ord-b69d4aead2744f77805804183feba95f
Source dataset
uspto-grants-2015_09
Patent number
US09120800B2

Reaction notes

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