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

HRID 2059202ノート

反応式

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]

参加物

反応物 3

HCID 7918Acetic Anhydride

HCID 5284603Oxycodone2 回

HCID 5489120Noroxycodone

生成物 1

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

実験手順

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.

出典と根拠

ORDレコード: ord-08bc049ccee843f08ff129046415ccb1
出典データセット: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04322426

反応ノート

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