(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 1790729Notes

Reaction equation

HRID 1790729 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]>[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

3

Reactant 1

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-one

Product 1

HCID 5284603OxycodoneYield 85%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To the solution of 14-hydroxycodeinone produced in Example 14 is added 0.5 g of 5% palladium on carbon, 50% wet. The mixture is hydrogenated at 30 to 40 psi for a period of 18 to 25 hours at ambient temperature. The catalyst is filtered off and is washed with 5 ml of water. The filtrate is cooled to 0–5° C. and with stirring, sufficient concentrated (28–30%) ammonium hydroxide is added to raise the pH to 10–12. The resulting suspension is stirred at 0–5° C. for 1–2 hours. The solid is filtered off and is washed with two 5 ml portions of water. The product is dried in vacuo (e.g., 50 mm Hg) at 30–40° C. to yield 8.1 g of oxycodone (85% yield based on thebaine bitartrate). The product purity is better than 98%.

Workup

  1. filtrationThe catalyst is filtered off
  2. washis washed with 5 ml of water
  3. temperatureThe filtrate is cooled to 0–5° C.
  4. concentrationsufficient concentrated (28–30%) ammonium hydroxide
  5. additionis added
  6. temperatureto raise the pH to 10–12
  7. stirringThe resulting suspension is stirred at 0–5° C. for 1–2 hours
  8. filtrationThe solid is filtered off
  9. washis washed with two 5 ml portions of water
  10. customThe product is dried in vacuo (e.g., 50 mm Hg) at 30–40° C.

Sources & evidence

ORD record
ord-190cfc1c9d394de69600f360139a158f
Source dataset
uspto-grants-2006_07
Patent number
US07071336B2

Reaction notes

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