Water → HCID 46781713, compound

HRID 578763Notes

Reaction equation

HRID 578763 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.CC(C)=O>[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

7

Reactant 3

HCID 962WaterHCID 5284570HydromorphoneHCID 546428064-31-3

Product 1

HCID 46781713HCID 46781713, compoundYield 84.5%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
81 °C

Procedure

A reaction flask was charged with morphine sulfate (40.0 g), water (30 mL), and EtOH (60 mL). 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 flask was charged with acetone (0.4 mL) and the catalyst (RuCl3.xH2O, 0.60 g). The reaction mixture was heated to reflux (80-82° C.) and maintained at that temperature for 24 h. HPLC analysis indicated that 93% (area) hydromorphone was formed. Acetonitrile (6 mL) was added to the reaction mixture and the mixture was heater under reflux for 2 h. EtOH (180 mL) was added to the mixture, which was then cooled down to 10° C. for 2 h. The mixture was filtered, and the solid was washed with 95% EtOH (3×15 mL). The solid was dried at 90° C. for 28 h to give 32.2 g of hydromorphone sulfate as solids (purity>98% 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 reaction mixture was heated
  5. temperaturemaintained at that temperature for 24 h
  6. customwas formed
  7. temperatureunder reflux for 2 h
  8. temperaturewas then cooled down to 10° C. for 2 h
  9. filtrationThe mixture was filtered
  10. washthe solid was washed with 95% EtOH (3×15 mL)
  11. customThe solid was dried at 90° C. for 28 h

Sources & evidence

ORD record
ord-fa64042b9a2d403881a13f6b86c2de75
Source dataset
uspto-grants-2015_05
Patent number
US09040705B2

Reaction notes

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