Hydrocodone → Codeine
反応式
[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]1参加物
6
実験手順
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.