Development of a photolabile amine protecting group suitable for multistep flow synthesis

Han Yueh; Anastasia Voevodin; Aaron B. Beeler

doi:10.1556/jfc-d-14-00016

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Journal of Flow Chemistry

Volume/Issue:: Volume 5: Issue 3

Development of a photolabile amine protecting group suitable for multistep flow synthesis

Authors:

Han Yueh

Han Yueh Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA

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Anastasia Voevodin

Anastasia Voevodin Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA

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Aaron B. Beeler

Aaron B. Beeler Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA

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Pages:: 155–159

Online Publication Date:: Sep 2015

Publication Date:: 01 Sep 2015

Article Category:: Research Article

DOI:: https://doi.org/10.1556/jfc-d-14-00016

Keywords:: photochemistry; flow chemistry; photolabile protecting group; multistep flow synthesis

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9-Hydroxymethylxanthene derivatives were optimized as a photolabile protecting group for amines in flow chemistry. 9-Methylxanthene and 2-methoxy-9-methylxanthene showed excellent deprotection yields in protic and aprotic solvents, respectively. The protecting group has good stability in acidic, basic, and thermal conditions and was successfully utilized for protection and deprotection of a variety of amines. A multistep continuous-flow synthesis of a piperazinylcarbonyl-piperidine derivative utilized the 2-methoxy-9-methylxanthene as the key protecting group utilized in an orthogonal manner.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)