An Efficient Method for the
Preparation of Versatile Building Blocks: 1-Substituted
2,2-Dimethoxyethylamine Hydrochlorides

Bo Liu; Deyong Su; Guolin Cheng; Hui Liu; Xinyan Wang; Yuefei Hu

doi:10.1055/s-0029-1216943

PAPER

An Efficient Method for the Preparation of Versatile Building Blocks: 1-Substituted 2,2-Dimethoxyethylamine Hydrochlorides

Bo Liu, Deyong Su, Guolin Cheng, Hui Liu, Xinyan Wang*, Yuefei Hu*
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China
Fax: +86(10)62771149; e-Mail: wangxinyan@mail.tsinghua.edu.cn; e-Mail: yfh@mail.tsinghua.edu.cn;

Abstract

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Abstract

A novel method for the preparation of 1-substituted 2,2-dimethoxyethylamine hydrochlorides was developed. The method includes three highly efficient steps: (1) direct use of aqueous (MeO)₂CHCHO for the preparation of N,O-acetal by condensation with Betti base without acidic catalyst; (2) regioselective alkylations of the N,O-acetal with Grignard reagents; and (3) Pd/C catalytic hydrogenolyses of benzylamines in the presence of ClCH₂CHCl₂ to directly give the target products as crystalline amine hydrochlorides. The method reported is extremely convenient and highly efficient with wide substrate scopes.

Key words

heterocycles - alkylation - N-debenzylation - Betti base - 2,2-dimethoxyethylamines

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Referenzen

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