Application of the PMC protecting group in the efficient synthesis of 4,4-disubstituted piperidines

被引：0

作者：

Ralbovsky, JL ^{[1
]}

Lisko, JG ^{[1
]}

He, W ^{[1
]}

机构：

[1] Johnson & Johnson Pharmaceut Res & Dev LLC, Drug Discovery, Spring House, PA 19477 USA

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 12期

关键词：

1,4-addition; 4,4-disubstituted piperidines; PMC protecting group;

D O I：

10.1081/SCC-200061570

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of the 4,4-disubstituted piperidine scaffold 1 was accomplished by treating the PMC N-protected alpha,beta-unsaturated ethyl cyanoacetate 9 with various Grignard reagents (R1MgX). Subsequent heating at 190 degrees C in a strong base provided carboxylic acids 12-20b in good yield. The PMC group was easily removed at room temperature with 33% HBr in acetic acid.

引用

页码：1613 / 1625

页数：13

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