AN ALTERNATIVE SYNTHESIS OF THE NMDA ANTAGONIST CGS-19755 VIA FREE-RADICAL CARBAMOYLATION OF ETHYL ISONICOTINATE

被引：8

作者：

MARTIN, I

ANVELT, J

VARES, L

KUHN, I

CLAESSON, A

机构：

[1] ASTRA PAIN CONTROL,PRECLIN RES,S-15185 SODERTALJE,SWEDEN

[2] INST CHEM,DEPT BIOORGAN CHEM,TALLINN 0026,ESTONIA

来源：

ACTA CHEMICA SCANDINAVICA | 1995年 / 49卷 / 03期

关键词：

D O I：

10.3891/acta.chem.scand.49-0230

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The NMDA antagonist CGS 19755 (cis-4-phosphonomethyl-2-piperidinecarboxylic acid) has been prepared by applying Minisci reaction conditions [formamide, hydrogen peroxide, iron(II) sulfate] to ethyl isonicotinate, reduction of the ester with sodium borohydride, alcoholysis of the 2-carboxamide, formation of 4-(diethylphosphonomethyl)-2-pyridinecarboxyl hydrogenation of the pyridine nucleus, and acid hydrolysis. The overall, unoptimized yield was around 11%. The procedure employs cheap starting materials, is practical and avoids the use of toxic and hazardous cyanotrimethylsilane which is used in the published procedure.

引用

页码：230 / 232

页数：3

共 5 条

[1] STRUCTURAL REQUIREMENTS FOR THE DEVELOPMENT OF POTENT N-METHYL-D-ASPARTIC ACID (NMDA) RECEPTOR ANTAGONISTS [J].