氨基硼氢化物。11. 使用氨基硼氢化锂将N-烷基内酰胺轻松还原为相应的胺。

Aminoborohydrides. 11. Facile reduction of N-alkyl lactams to the corresponding amines using lithium aminoborohydrides.

作者信息

Flaniken J M, Collins C J, Lanz M, Singaram B

机构信息

Department of Chemistry and Biochemistry, University of California at Santa Cruz, Santa Cruz, California 95064, USA.

出版信息

Org Lett. 1999 Sep 9;1(5):799-801. doi: 10.1021/ol990145e.

DOI:10.1021/ol990145e

PMID:16118886

Abstract

[reaction: see text] Various five- and six-membered N-alkyl lactams were reduced to the corresponding cyclic amines using lithium N,N-dialkylaminoborohydrides (LAB). Most of the reductions were essentially complete after refluxing in THF for 2 h. The cyclic amine products were easily isolated after an aqueous workup in very good to excellent yields. It is possible to selectively reduce most functional groups, such as esters, in the presence of a lactam using LAB reagents.

摘要

[反应：见正文] 使用N，N-二烷基氨基硼氢化锂（LAB）将各种五元及六元N-烷基内酰胺还原为相应的环胺。在四氢呋喃（THF）中回流2小时后，大多数还原反应基本完成。经水相后处理，环胺产物易于分离，产率很高至极高。使用LAB试剂，有可能在存在内酰胺的情况下选择性还原大多数官能团，如酯基。