3-Methoxynaltrexone → Naltrexone

HRID 971918Notes

Reaction equation

HRID 971918 reaction equation
C[O:2][C:3]1[CH:26]=[CH:25][C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14][CH:15]4[CH2:17][CH2:16]4)[CH2:12][CH2:11][C@:10]45[C@H:18]([C:20]([CH2:22][CH2:23][C@@:9]34[OH:24])=[O:21])[O:19][C:4]=1[C:5]=25.[CH:27]1([CH2:30][N:31]2[CH2:49][CH2:48][C@@:38]34[C:39]5[CH:40]=[C:41]([O:46]C)[CH:42]=[CH:43][C:44]=5[CH2:45][C@@H:32]2[C@:33]3([OH:50])[CH2:34][CH2:35][CH2:36][CH2:37]4)[CH2:29][CH2:28]1.[CH:51]1([CH2:55][N:56]2[CH2:74][CH2:73][C@@:63]34[C:64]5[CH:65]=[C:66]([O:71]C)[CH:67]=[CH:68][C:69]=5[CH2:70][C@@H:57]2[C@:58]3([OH:76])[CH2:59][CH2:60][C:61](=[O:75])[CH2:62]4)[CH2:54][CH2:53][CH2:52]1>>[CH2:16]1[CH:15]([CH2:14][N:13]2[C@@H:8]3[CH2:7][C:6]4[CH:25]=[CH:26][C:3]([OH:2])=[C:4]5[O:19][C@H:18]6[C:20]([CH2:22][CH2:23][C@:9]3([OH:24])[C@:10]6([C:5]=45)[CH2:11][CH2:12]2)=[O:21])[CH2:17]1.[CH:27]1([CH2:30][N:31]2[CH2:49][CH2:48][C@@:38]34[C:39]5[CH:40]=[C:41]([OH:46])[CH:42]=[CH:43][C:44]=5[CH2:45][C@@H:32]2[C@:33]3([OH:50])[CH2:34][CH2:35][CH2:36][CH2:37]4)[CH2:29][CH2:28]1.[CH:51]1([CH2:55][N:56]2[CH2:74][CH2:73][C@@:63]34[C:64]5[CH:65]=[C:66]([OH:71])[CH:67]=[CH:68][C:69]=5[CH2:70][C@@H:57]2[C@:58]3([OH:76])[CH2:59][CH2:60][C:61](=[O:75])[CH2:62]4)[CH2:52][CH2:53][CH2:54]1

Participants

6

Reactant 3

HCID 54876953-MethoxynaltrexoneHCID 57257006(-)-3-Methoxy-6-oxo ButorphanolHCID 70587809N-cyclopropylmethyl-3-methoxy-14-hydroxymorphinan

Product 3

HCID 5360515NaltrexoneHCID 5361090OxilorphanHCID 570886446-Oxo (-)-Butorphanol

Procedure

In accordance with the above procedure, but starting, in place of N-cyclobutylmethylnoroxycodone, with N-cyclopropylmethylnoroxycodone (6a), N-ethylnoroxycodone (6c), N-cyclopropylmethyl-3-methoxy-14-hydroxymorphinan (6e), or N-cyclobutylmethyl-3-methoxy-14-hydroxy-6-oxomorphinan (6f), there is obtained the corresponding N-cyclopropylmethylnoroxymorphone (7a), N-ethylnoroxymorphone (7c), N-cyclopropylmethyl-3,14-dihydroxymorphinan (7e) or N-cyclobutylmethyl-3,14-dihydroxy-6-oxomorphinan (7f).

Sources & evidence

ORD record
ord-cebc1ec4a2e44d4098f1852fd0a5ec36
Source dataset
uspto-grants-1979_07
Patent number
US04161597

Reaction notes

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