(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 1436847Notes

Reaction equation

HRID 1436847 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]>C(O)(=O)C.[Pd].O>[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 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

72.50 kg of 14-Hydroxycodeinone is dissolved in 10% aqueous solution of acetic acid, 5% Pd/C catalyst is added, and the mixture is hydrogenated under overpressure of electrolytic hydrogen 104 to 106 kPa at temperatures 30 to 35° C. The reaction mixture is diluted with 200 l of water, filtered, the filtrate is cooled down to 5° C. and Oxycodone base is precipitated by adjusting pH with an addition of an ethanolic solution of ammonia to the value 9.2. The suspension is centrifuged, Oxycodone is washed with water and dried at 70 to 80° C. At least 67 kg (92%, purity 98.5%) of Oxycodone is obtained.

Workup

  1. additionis added
  2. filtrationfiltered
  3. customOxycodone base is precipitated
  4. additionwith an addition of an ethanolic solution of ammonia to the value 9.2
  5. washOxycodone is washed with water
  6. customdried at 70 to 80° C

Sources & evidence

ORD record
ord-2d72060a678044c190f36b7e33888f35
Source dataset
uspto-grants-2009_11
Patent number
US07619087B2

Reaction notes

Loading…