Hydrogen Peroxide → (4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

HRID 254842

反応式

HRID 254842 の反応式
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5C(OC)=CC=C2[C@]5(C=34)CC1.[O-]C(C(C(C(O)=O)O)O)=O.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5C(C=C[C@@H]2[C@]5(C=34)CC1)=O.OO.C(OO)(=O)C>C(O)=O.C(O)(C)C>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][CH:13]5[C:14]([CH:16]=[CH:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

参加物

8

反応物 5

HCID 784Hydrogen PeroxideHCID 6585Peracetic AcidHCID 5284603Oxycodone2 回HCID 5459910CodeinoneHCID 131728625(4R,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline;2,3,4-trihydroxy-4-oxobutanoate

生成物 1

HCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 3776Isopropanol溶媒

実験手順

Oxycodone has also been prepared from thebaine bitartrate and codeinone ethyldienol ether by oxidation with hydrogen peroxide in formic acid and isopropanol, followed by catalytic hydrogenation5. Oxycodone has also been prepared by the oxidation with peracetic acid of codeinone dienol silylether in organic solvents to give 14-hydroxycodeinone, followed by catalytic hydrogenation in acetic acid solution15.

出典と根拠

ORDレコード
ord-4a9bcdf3242041dfa8552b1c331e322b
出典データセット
uspto-grants-2011_01
特許番号
US07875719B2

関連ノート

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