Oxycodone → Oxycodone

HRID 2369250Notes

Reaction equation

HRID 2369250 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[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]>C(O)C>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[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].[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][CH:13]5[C:14]([CH:16]=[CH:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

4

Reactant 1

HCID 5284603Oxycodone

Product 2

HCID 5284603OxycodoneHCID 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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 50 mL flask was charged 3.986 g (12.64 mmoles) of low ABUK oxycodone base prepared by combining the sample from Examples 8 and 8A (purified via hydrogenation) (composite: 2 ppm 8α,14-dihydroxy-7,8-dihydrocodeinone, 35 ppm 8α,14-dihydroxy-7,8-dihydrocodeinone, 1.06A % 6-oxycodol, 98.42A % pure by HPLC) and 24 mL of denatured ethanol (SDA3A). The mixture (slurry) was heated to reflux for 1.5 h, cooled to RT, and then 0-5° C. Solid was isolated by filtration, rinsed and dried. 3.307 g of purified low ABUK oxycodone base was obtained (2.7 ppm 14-hydroxycodeinone, undetected 8α,14-dihydroxy-7,8-dihydrocodeinone by LC/MS, 11 ppm 8β,14-dihydroxy-7,8-dihydrocodeinone by LC/MS, 0.21 HPLC A % 6-oxycodol; 99.71A % pure by HPLC).

Workup

  1. customprepared
  2. temperatureThe mixture (slurry) was heated
  3. temperatureto reflux for 1.5 h
  4. custom0-5° C
  5. customSolid was isolated by filtration
  6. washrinsed
  7. customdried

Sources & evidence

ORD record
ord-a5bcbe5e9d3f466bbfe09108e1737987
Source dataset
uspto-grants-2014_04
Patent number
US08703950B2

Reaction notes

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