Water → Oxymorphone

HRID 1673060Notes

Reaction equation

HRID 1673060 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22]C)=[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]=34)[CH2:4][CH2:3]1)=[O:15].B(Br)(Br)Br.O>C(Cl)(Cl)Cl>[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]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 5284603Oxycodone

Product 1

HCID 5284604Oxymorphone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Oxycodone (10.0 g) was suspended in chloroform (CHCl3, 150 mL) in a reactor A. Boron tribromide (BBr3, 10.0 mL) was added slowly and an exotherm was observed. The reaction temperature was maintained below 25° C. during the addition. Stirring of the mixture was continued at room temperature for 14 hours. The material was transferred to reactor B that was pre-filled with 85 mL of water. The temperature reached 50 to 55° C. and was maintained below 55° C. during the addition. After transfer of the mixture to reactor B, some solid residue still remained in reactor A. The mixture in reactor B was stirred at 50 to 55° C. to dissolve the solid (about 15 minutes) and then when stirring was stopped, the mixture separated into two clear layers. The aqueous solution in reactor B was transferred back to reactor A. The mixture was stirred at 50 to 55° C. for 15 to 30 minutes to dissolve all the solids. The organic layer in reactor B was extracted with H3PO4/H2O solution (2% wt/wt, 15 mL). The aqueous extraction was transferred to reactor A. The solution in reactor A was extracted with dichloroethane (30 mL) and then allowed to separate into two phases.

Workup

  1. temperatureThe reaction temperature was maintained below 25° C. during the addition
  2. customThe material was transferred to reactor
  3. customreached 50 to 55° C.
  4. temperaturewas maintained below 55° C. during the addition
  5. customAfter transfer of the mixture to reactor B, some solid residue still remained in reactor
  6. stirringThe mixture in reactor B was stirred at 50 to 55° C.
  7. dissolutionto dissolve the solid (about 15 minutes)
  8. stirringwhen stirring
  9. customthe mixture separated into two clear layers
  10. customThe aqueous solution in reactor B was transferred back to reactor
  11. stirringThe mixture was stirred at 50 to 55° C. for 15 to 30 minutes
  12. dissolutionto dissolve all the solids
  13. extractionThe organic layer in reactor B was extracted with H3PO4/H2O solution (2% wt/wt, 15 mL)
  14. extractionThe aqueous extraction
  15. customwas transferred to reactor
  16. extractionThe solution in reactor A was extracted with dichloroethane (30 mL)
  17. customto separate into two phases

Sources & evidence

ORD record
ord-9a16e540bab44bb08ae18f98c10e06ab
Source dataset
uspto-grants-2011_08
Patent number
US07999105B2

Reaction notes

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