Water → HCID 46781713, compound

HRID 578764Notes

Reaction equation

HRID 578764 reaction equation
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH:6]1[C:22]2[CH2:21][C@H:20]3[N:23]([CH2:25][CH2:26][C@@:12]45[C@H:19]3[CH:18]=[CH:17][C@H:15]([OH:16])[C@@H:13]4[O:14][C:10]([C:11]=25)=[C:8](O)[CH:7]=1)[CH3:24].O.CN1[C@@H]2CC3=CC=C(O)C4O[C@H]5C(CC[C@@H]2[C@]5(C=43)CC1)=O>CCO.C(#N)C>[CH3:24][N:23]1[C@@H:20]2[CH2:21][C:22]3=[CH:6][CH:7]=[C:8]([O:2][S:1]([OH:5])(=[O:4])=[O:3])[C:10]4[O:14][C@H:13]5[C:15]([CH2:17][CH2:18][C@@H:19]2[C@:12]5([C:11]=43)[CH2:26][CH2:25]1)=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 5284570HydromorphoneHCID 546428064-31-3

Product 1

HCID 46781713HCID 46781713, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
81 °C

Procedure

Morphine sulfate (30.0 g), water (30 mL), and EtOH (60 mL) were added to a reaction flask. The reaction mixture was agitated to form a suspension. The reactor was flushed with nitrogen and the reaction mixture was kept under nitrogen throughout the reaction. The reaction flask was charged with the catalyst (RuCl3.xH2O, 0.60 g), and the mixture was heated to reflux (80-82° C.) for 16 h. HPLC analysis indicated that 94.5% (area) hydromorphone was formed. Acetonitrile (30 mL) was added to the reaction mixture and the mixture was heated for 1 h. EtOH (90 mL) was added to the mixture, which was then cooled to 15° C. for 2 h. The mixture was filtered, and the solid was washed with 95% EtOH (2×15 mL). The solid was dried under vacuum at 65° C. for 18 h to give 13.8 g of hydromorphone sulfate as solids (purity>99% area).

Workup

  1. customto form a suspension
  2. customThe reactor was flushed with nitrogen
  3. customthe reaction mixture was kept under nitrogen throughout the reaction
  4. temperaturethe mixture was heated
  5. customwas formed
  6. temperaturethe mixture was heated for 1 h
  7. temperaturewas then cooled to 15° C. for 2 h
  8. filtrationThe mixture was filtered
  9. washthe solid was washed with 95% EtOH (2×15 mL)
  10. customThe solid was dried under vacuum at 65° C. for 18 h

Sources & evidence

ORD record
ord-da674fde114845cd8707fd845d0c2220
Source dataset
uspto-grants-2015_05
Patent number
US09040705B2

Reaction notes

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