(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one → Oxycodone

HRID 860770Notes

Reaction equation

HRID 860770 reaction equation
[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]4[O:22][CH:6]5[C:7]([CH:9]=[CH:10][C@:11]2([OH:23])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].[H][H]>O.C(O)(=O)C.[Pd]>[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]4[O:22][C@H:6]5[C:7]([CH2:9][CH2:10][C@:11]2([OH:23])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8]

Participants

6

Reactant 2

HCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 5284603OxycodoneYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The 14-hydroxycodeinone (39.45 g of the damp solid) was dissolved in water (81.13 ml) and 80% acetic acid (16.17 ml). 10 wt % palladium on carbon catalyst (0.33 g wet weight, 0.16 g dry weight) was added and hydrogen was passed through the mixture for about 6 hours at about 12 psi. The mixture was filtered to remove the catalyst. An ammonium hydroxide solution was added to the mixture up to pH 9. The solid precipitate was washed with water and with ethanol, and was dried. The product was oxycodone (18.8 g, 79% yield).

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. additionAn ammonium hydroxide solution was added to the mixture up to pH 9
  4. washThe solid precipitate was washed with water and with ethanol
  5. customwas dried

Sources & evidence

ORD record
ord-adfaa28c5fb94177ad501ed17e44809d
Source dataset
uspto-grants-2006_12
Patent number
US07153966B2

Reaction notes

Loading…