Efficient and scalable method for the selective alkylation and acylation of secondary amines in the presence of primary amines | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

7856183

Reference Type

Journal Article

Title

Efficient and scalable method for the selective alkylation and acylation of secondary amines in the presence of primary amines

Author(s)

Laduron, F; Tamborowski, V; Moens, L; Horvath, A; De Smaele, D; Leurs, S

Year

2005

Is Peer Reviewed?

Journal

Organic Process Research and Development
ISSN: 1083-6160

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

Volume

Issue

Page Numbers

102-104

Language

English

DOI

10.1021/op049812w

Web of Science Id

WOS:000226568000014

Abstract

Selective substitution of secondary amines in the presence of primary amines is performed by using the reaction solvent, methyl isobutylketone (MIBK), as a temporary protecting group for the primary amine. After acylation or alkylation of the secondary amine, the resulting imine intermediate is smoothly hydrolysed, leading to the free primary amine in high yield and purity. This procedure represents a cheap and scalable alternative to multistep methods requiring several protections and deprotections.