Oxycodone → Oxycodone

HRID 1391281노트

반응식

[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]

참가 물질

반응물 5

HCID 5284603Oxycodone

HCID 5360515Naltrexone2회

HCID 54876953-Methoxynaltrexone

HCID 5489120Noroxycodone

HCID 1528625314-Hydroxymorphine-6-one

생성물 2

HCID 5284603Oxycodone

HCID 5284604Oxymorphone

실험 절차

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.

출처 및 근거

ORD 기록: ord-4d852c20e85a470898c60d29ac637275
출처 데이터셋: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04141897

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