HYDROXYLATED METABOLITES OF LORATADINE - AN EXAMPLE OF CONFORMATIONAL DIASTEREOMERS DUE TO ATROPISOMERISM

被引：30

作者：

PIWINSKI, JJ

WONG, JK

CHAN, TM

GREEN, MJ

GANGULY, AK

机构：

[1] Schering-Plough Research, Schering-Plough Corporation, Bloomfield, New Jersey 07003

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The structures of two metabolites of the nonsedating antihistamine loratadine (1) were confirmed by synthesis. The metabolites 3a and 3b, which are hydroxylated in the bridgehead, were each prepared from tricyclic ketone 8 in seven steps. Each of these compounds was found to exist as a pair of conformational diastereomers which interconvert slowly at room temperature. These conformers arise due to the restricted conformational mobility inherent to the diaryl [a, d]cycloheptane ring system. © 1990, American Chemical Society. All rights reserved.

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页码：3341 / 3350

页数：10

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