反応 #342024

ord-4a9bcdf3242041dfa8552b1c331e322b

反応方程式

COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
Oxycodone
COC1=CC=C2[C@H]3Cc4ccc(OC)c5c4[C@@]2(CCN3C)[C@H]1O5.O=C([O-])C(O)C(O)C(=O)O
thebaine bitartrate
COc1ccc2c3c1O[C@H]1C(=O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314
codeinone
OO
hydrogen peroxide
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
Oxycodone
CC(=O)OO
peracetic acid
→
COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
14-hydroxycodeinone

反応物

COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
Oxycodone
COC1=CC=C2[C@H]3Cc4ccc(OC)c5c4[C@@]2(CCN3C)[C@H]1O5.O=C([O-])C(O)C(O)C(=O)O
thebaine bitartrate
COc1ccc2c3c1O[C@H]1C(=O)C=C[C@H]4[C@@H](C2)N(C)CC[C@]314
codeinone
OO
hydrogen peroxide
—
codeinone dienol silylether
COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
Oxycodone
CC(=O)OO
peracetic acid

試薬

なし

溶媒

O=CO
formic acid
CC(C)O
isopropanol

反応条件

詳細条件
See reaction.notes.procedure_details.

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

DOI: 10.6084/m9.figshare.5104873.v1特許: US07875719B2uspto-grants-2011_01