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

Title
Selective Ring-Opening of N-Alkyl Pyrrolidines with Chloroformates to 4-Chlorobutyl Carbamates
Authors
Yu, ChunghyeonShoaib, Mahbubul AlamIqbal, NaeemKim, Jun SooHa, Hyun-JoonCho, Eun Jin
Ewha Authors
김준수
SCOPUS Author ID
김준수scopus
Issue Date
2017
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263JCR Link
Citation
vol. 82, no. 13, pp. 6615 - 6620
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS scopus
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.
DOI
10.1021/acs.joc.7b00681
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자연과학대학 > 화학·나노과학전공 > Journal papers
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