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Hydrocodone → Codeine

HRID 496801
Notes
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Reaction equation

HRID 496801 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[CH3:23][N:24]1[C@@H:41]2[CH2:42][C:29]3[CH:30]=[CH:31][C:32]([O:43][CH3:44])=[C:33]4[O:34][C@H:35]5[C:36]([CH:38]=[CH:39][C@@H:40]2[C@:27]5([C:28]=34)[CH2:26][CH2:25]1)=[O:37].[CH3:45][N:46]1[C@@H:62]2[CH2:63][C:51]3[CH:52]=[CH:53][C:54]([O:66][CH3:67])=[C:55]4[O:56][C@H:57]5[C:58]([O:64][CH3:65])=[CH:59][CH:60]=[C:61]2[C@:49]5([C:50]=34)[CH2:48][CH2:47]1>>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH:16]=[CH:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].[CH3:23][N:24]1[C@@H:41]2[CH2:42][C:29]3[CH:30]=[CH:31][C:32]([O:43][CH3:44])=[C:33]4[O:34][C@H:35]5[C@@H:36]([OH:37])[CH:38]=[CH:39][C@@H:40]2[C@:27]5([C:28]=34)[CH2:26][CH2:25]1.[CH3:45][N:46]1[C@@H:62]2[CH2:63][C:51]3[CH:52]=[CH:53][C:54]([O:66][CH3:67])=[C:55]4[O:56][C@H:57]5[C:58]([O:64][CH3:65])=[CH:59][CH:60]=[C:61]2[C@:49]5([C:50]=34)[CH2:48][CH2:47]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5284569HydrocodoneHCID 5324289ThebaineHCID 5459910Codeinone

Product 3

HCID 5284371CodeineHCID 5324289ThebaineHCID 5459910Codeinone

Procedure

Hydrocodone has been prepared by reduction of codeinone (Arch. Pharm (1920), 258, 295; J. Am Chem. Soc (1950), 72, 3247, U.S. Pat. No. 5,571,685) or thebaine (DE Pat. No. 441,613). However, since codeinone is obtained by oxidation of codeine in low to moderate yields, and thebaine is a relatively scarce alkaloid, these methods have little practical value.

Sources & evidence

ORD record
ord-c46228bdbd2a46d990394e87ee0a0f24
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06946556B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes