The Barton reaction using a microreactor and black light. Continuous-flow synthesis of a key steroid intermediate for an endothelin receptor antagonist

Atsushi Sugimoto, Yukihito Sumino, Makoto Takagi, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

72 Scopus citations

Abstract

The Barton reaction (nitrite photolysis) of a steroidal substrate 1, to give 2, a key intermediate for the synthesis of an endothelin receptor antagonist, was successfully carried out in a continuous microflow system using a pyrex glass-covered stainless-steel microreactor having a microchannel (Type A: 1000 μm width, 107 μm depth, 2.2 m length). We found that a 15 W black light (peak wavelength: 352 nm) as the light source, suffices for the Barton reaction, creating a compact photo-micro reaction system. Multi-gram scale production was attained using two serially connected, multi-lane microreactors (Type B).

Original languageEnglish
Pages (from-to)6197-6200
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number35
DOIs
StatePublished - 28 Aug 2006

Keywords

  • Barton reaction
  • Black light
  • Continuous microflow synthesis
  • Endothelin receptor antagonist
  • Microreactor

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