Acetic Anhydride → (5alpha,14alpha)-3-Methoxy-17-methyl-6-oxo-4,5-epoxymorphinan-14-yl acetate

HRID 2059202Notes

Reaction equation

C[O:2][C:3]1C=CC2C[C@H]3NCC[C@]45[C@H](C(CC[C@@]34O)=O)O[C:4]=1C=25.[CH3:23][N:24]1[C@@H:41]2[CH2:42][C:29]3[CH:30]=[CH:31][C:32]([O:44][CH3:45])=[C:33]4[O:34][C@H:35]5[C:36]([CH2:38][CH2:39][C@:40]2([OH:43])[C@:27]5([C:28]=34)[CH2:26][CH2:25]1)=[O:37].C(OC(=O)C)(=O)C>>[CH3:4][C:3]([O:43][C@@:40]12[C@H:41]3[CH2:42][C:29]4[CH:30]=[CH:31][C:32]([O:44][CH3:45])=[C:33]5[O:34][C@H:35]([C@@:27]1([C:28]=45)[CH2:26][CH2:25][N:24]3[CH3:23])[C:36](=[O:37])[CH2:38][CH2:39]2)=[O:2]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 5284603Oxycodone2×

HCID 5489120Noroxycodone

Product 1

HCID 13034605(5alpha,14alpha)-3-Methoxy-17-methyl-6-oxo-4,5-epoxymorphinan-14-yl acetate

Procedure

The noroxycodone used as starting material for Method II is prepared from oxycodone by the following steps: ##STR13## Oxycodone is refluxed with acetic anhydride to yield 14-acetyloxycodone. This product is reacted with cyanogen bromide to yield 14-acetyloxy-17-cyano-7,8-dihydronorcodone which is in turn converted to noroxycodone by reaction with hydrogen chloride. The oxycodone starting material is prepared according to M. Freund and E. Speyer, J. fur Praktische Chemie, 94, 135-137 (1916), the disclosure of which is hereby incorporated by reference.

Sources & evidence

ORD record: ord-08bc049ccee843f08ff129046415ccb1
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04322426

Reaction notes

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