Oxycodone → Oxycodone

反応式

[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]

参加物

反応物 5

HCID 5284603Oxycodone

HCID 5360515Naltrexone2 回

HCID 54876953-Methoxynaltrexone

HCID 5489120Noroxycodone

HCID 1528625314-Hydroxymorphine-6-one

生成物 2

HCID 5284603Oxycodone

HCID 5284604Oxymorphone

実験手順

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.

出典と根拠

ORDレコード: ord-4d852c20e85a470898c60d29ac637275
出典データセット: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04141897

反応ノート

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