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HRID1391281

反应详情

EQUATION

反应方程式

HRID 1391281 的结构方程式

REACTANTS

反应物

5
结构：COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
HCID5284603

Oxycodone

C18H21NO4

结构：O=C1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
HCID5360515

Naltrexone

C20H23NO4

2 次

结构：COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(CC2CC2)CC[C@]314
HCID5487695

17-(Cyclopropylmethyl)-14-hydroxy-3-methoxy-4,5-epoxymorphinan-6-one

C21H25NO4

结构：COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)NCC[C@]314
HCID5489120

未命名化合物

结构：CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)C=C[C@@]3(O)[C@H]1C5
HCID15286253

未命名化合物

PRODUCTS

生成物

2
结构：COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314
HCID5284603

Oxycodone

C18H21NO4

结构：CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
HCID5284604

(-)-Oxymorphone

C17H19NO4

PROCEDURE

实验过程

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.