Hydrochloric Acid → Oxycodone

HRID 1406625Notes

Reaction equation

Cl.[CH3:2][N:3]1[C@@H:13]2[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]4[O:23][CH:7]5[C:8]([CH:10]=[CH:11][C@:12]2([OH:24])[C@:6]5([C:16]=34)[CH2:5][CH2:4]1)=[O:9].CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5C(C=C[C@@H]2[C@]5(C=34)CC1)=O>>[CH3:2][N:3]1[C@@H:13]2[CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]4[O:23][C@H:7]5[C:8]([CH2:10][CH2:11][C@:12]2([OH:24])[C@:6]5([C:16]=34)[CH2:5][CH2:4]1)=[O:9]

Participants

Reactant 3

HCID 313Hydrochloric Acid

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

HCID 5459910Codeinone

Product 1

HCID 5284603Oxycodone

Procedure

A blank 0.1 M HCl, 0.25 mg/mL standards of 14-hydroxycodeinone and codeinone, 0.58 μg/mL and 0.58 μg/mL of an oxycodol in 0.1M HCL standard were prepared and then analysed using the above method. ˜1 mg/mL samples of the post hydrogenation liquors and isolated oxycodone alkaloid were also prepared in 0.1M HCl.

Sources & evidence

ORD record: ord-d9513ed4fb174f6e98b9c59c4af3489f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916707B2

Reaction notes

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