An Improved Process for the N-Demethylation of Opiate Alkaloids using an Iron(II) Catalyst in Acetate Buffer

被引：38

作者：

Kok, Gaik ^{[1
]}

Ashton, Trent D. ^{[1
]}

Scammells, Peter J. ^{[1
]}

机构：

[1] Monash Univ, Monash Inst Pharmaceut Sci, Parkville, Vic 3052, Australia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 1-2期

关键词：

alkaloids; amine N-oxides; iron(II) porphyrins; N-demethylation; Polonovski reaction; NONCLASSICAL POLONOVSKI REACTION; MUCOR PIRIFORMIS; THEBAINE; MORPHINE; CODEINE;

D O I：

10.1002/adsc.200800632

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An improved process to N-demethylate opiate alkaloids utilising a solution of the ferrous porphyrin, tetrasodium 5,10,15,20-tetra(4-sulfophenyl)porphyrinatoiron(II) [=Fe(II)-TPPS (8)], in acetate buffer is described. This method provided the corresponding N-demethylated opiates in good yield with high reproducibility.

引用

页码：283 / 286

页数：4

共 20 条

[1]

BARRY JE, 1974, J ORG CHEM, V39, P3488

[2]

Caldwell GW, 1996, MAGN RESON CHEM, V34, P505, DOI 10.1002/(SICI)1097-458X(199607)34:7<505::AID-OMR913>3.0.CO

[3]

2-Y

[4]

COOLEY JH, 1989, SYNTHESIS-STUTTGART, P1

[5] New methodology for the N-demethylation of opiate alkaloids [J].

Dong, Zemin ;

Scammells, Peter J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :9881-9885

[6]

FRIES DS, 2002, FOYES PRINCIPLES MED

[7] A heme-like, water-soluble iron(II) porphyrin:: thermal and photoinduced properties, evidence for sitting-atop structure [J].

Huszánk, R ;

Horváth, O .

CHEMICAL COMMUNICATIONS, 2005, (02) :224-226

[8] MUCOR PIRIFORMIS, AN EFFICIENT N-DEALKYLATING REAGENT FOR THEBAINE AND ITS N-VARIANTS [J].

MADYASTHA, KM ;

REDDY, GVB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (08) :911-912

[9]

MADYASTHA KM, 1994, P INDIAN AS-CHEM SCI, V106, P1203

[10] Efficient N-demethylation of opiate alkaloids using a modified nonclassical Polonovski reaction [J].

McCamley, K ;

Ripper, JA ;

Singer, RD ;

Scammells, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9847-9850

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