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J Org Chem. 2017 Jul 7;82(13):6615-6620. doi: 10.1021/acs.joc.7b00681. Epub 2017 Jun 15.

Selective Ring-Opening of N-Alkyl Pyrrolidines with Chloroformates to 4-Chlorobutyl Carbamates.

Author information

1
Department of Bionanotechnology, Hanyang University , Ansan 15588, Republic of Korea.
2
Department of Chemistry & Nanoscience, Ewha Womans University , Seoul 03760, Republic of Korea.
3
National Institute of Biotechnology and Genetic Engineering , Faisalabad 38000, Pakistan.
4
Department of Chemistry, Hankuk University of Foreign Studies , Yongin 17053, Republic of Korea.
5
Department of Chemistry, Chung-Ang University , Seoul 06974, Republic of Korea.

Abstract

Our study shows that among aza-heterocycles of various ring sizes, including aziridines, azetidines, pyrrolidines, and piperidines, only N-alkyl pyrrolidines undergo competitive reaction pathways with chloroformates to yield N-dealkylated pyrrolidines and 4-chlorobutyl carbamates. The pathway taken depends on the substituent on the nitrogen, i.e., ring-opening with methyl and ethyl substituents and dealkylation with a benzyl substituent. Computational calculations support the substituent-dependent product formation by showing the energy difference between the transition states of both reaction pathways. Selective ring-opening reactions of N-methyl and N-ethyl pyrrolidine derivatives with chloroformates were utilized to prepare various 4-chlorobutyl carbamate derivatives as valuable 1,4-bifunctional compounds.

PMID:
28593764
DOI:
10.1021/acs.joc.7b00681

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