Journal of Flow Chemistry

, Volume 5, Issue 3, pp 155–159 | Cite as

Development of a Photolabile Amine Protecting Group Suitable for Multistep Flow Synthesis

Full Paper


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.


photochemistry flow chemistry photolabile protecting group multistep flow synthesis 

Supplementary material

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Supplementary material, approximately 1966 KB.


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Copyright information

© Akadémiai Kiadó 2015

Authors and Affiliations

  • Han Yueh
    • 1
  • Anastasia Voevodin
    • 1
  • Aaron B. Beeler
    • 1
  1. 1.Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU)Boston UniversityBostonUSA

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