Oxycodone → Oxycodone
Reaction equation
[CH:1]1[C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14]C4CC4)[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]([C:5]=25)=[C:3]([OH:25])[CH:2]=1.COC1C=CC2C[C@H]3NCC[C@]45[C@H](C(CC[C@@]34O)=O)OC=1C=25.[CH3:48][O:49][C:50]1[CH:73]=[CH:72][C:53]2[CH2:54][C@H:55]3[N:60]([CH2:61]C4CC4)[CH2:59][CH2:58][C@:57]45[C@H:65]([C:67]([CH2:69][CH2:70][C@@:56]34[OH:71])=[O:68])[O:66][C:51]=1[C:52]=25.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5C(CC[C@]2(O)[C@]5(C=34)CC1)=O.CN1[C@@H]2CC3C=CC(O)=C4O[C@H]5C(C=C[C@]2(O)[C@]5(C=34)CC1)=O>>[CH3:61][N:60]1[C@@H:55]2[CH2:54][C:53]3[CH:72]=[CH:73][C:50]([O:49][CH3:48])=[C:51]4[O:66][C@H:65]5[C:67]([CH2:69][CH2:70][C@:56]2([OH:71])[C@:57]5([C:52]=34)[CH2:58][CH2:59]1)=[O:68].[CH3:14][N:13]1[C@@H:8]2[CH2:7][C:6]3=[CH:1][CH:2]=[C:3]([OH:25])[C:4]4[O:19][C@H:18]5[C:20]([CH2:22][CH2:23][C@:9]2([OH:24])[C@:10]5([C:5]=43)[CH2:11][CH2:12]1)=[O:21]Participants
7
Procedure
It has been our surprising finding that making naltrexone via noroxycodone and N-cyclopropylmethylnoroxycodone is more efficient (circa 54% overall from oxycodone) than proceeding via noroxymorphone to naltrexone even when produced by the novel procedures of the present invention (43% overall from oxycodone via oxymorphone). Both procedures are more than twice as efficient as the procedures of the art which produce noroxymorphone from oxycodone via oxymorphone (Seki, Takamine Kenkyusho Nempo, 12, 56 (1960)), which proceed in an overall yield of about 21%. A third procedure for the synthesis of naltrexone is set forth in Applicant's co-pending application filed concurrently herewith.
Sources & evidence
- ORD record
- ord-4d852c20e85a470898c60d29ac637275
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04141897
Reaction notes
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