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

Chunghyeon Yu, Mahbubul Alam Shoaib, Naeem Iqbal, Jun Soo Kim, Hyun Joon Ha, Eun Jin Cho

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

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.

Original languageEnglish
Pages (from-to)6615-6620
Number of pages6
JournalJournal of Organic Chemistry
Volume82
Issue number13
DOIs
StatePublished - 7 Jul 2017

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

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