Details

Autor(en) / Beteiligte

• Kohrt, Jeffrey T
• Dorff, Peter H
• Burns, Michael
• Lee, Chewah
• O’Neil, Steven V
• Maguire, Robert J
• Kumar, Rajesh
• Wagenaar, Melissa
• Price, Loren
• Lall, Manjinder S

Titel

Application of Flow and Biocatalytic Transaminase Technology for the Synthesis of a 1‑Oxa-8-azaspiro[4.5]decan-3-amine

Ist Teil von

• Organic process research & development, 2022-03, Vol.26 (3), p.616-623

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Spirocyclic ring systems are useful intermediates in the design and synthesis of medicinally active agents and commonly found as cores in natural products. Recently, syntheses of a key intermediate Boc-protected-1-oxa-8-azaspiro[4.5]­decan-3-amine 1 were examined. While multigram quantities of the racemic material could be made from the reduction of an energic azide intermediate, larger scale reactions and a chiral synthesis required further investigations. Herein, we describe the use of a continuous three-step flow process to scale the formation and reduction of an azide intermediate, and the use of a transaminase to prepare the desired enantiomer in high yield and enantiomeric excess.