Resolution of 3-(methylamino)-1-(2-thienyl)propan-1-ol, a new key intermediate for duloxetine, with (S)-mandelic acid

• Sakai, Kenichi

• Sakurai, Rumiko

• Yuzawa, Atsushi

• Kobayashi, Yuka

• Saigo, Kazuhiko

抄録

The resolution of racemic 3-(methylamino)-1-(2-thienyl)propan-1-ol (3), a new key intermediate for duloxetine (1), was studied. The conditions were optimized for an industrial-scale resolution of 3 by using (S)-mandelic acid (4) as a resolving agent and 2-butanol containing two equimolar amounts of water as a solvent. The (S)-3･(S)-4･H2O diastereomeric salt was crystallized to give pure (S)-3 with >99.9% ee after liberation of the amine. Absolute configuration of liberated (-)-3 was determined as (S)-form by X-ray crystallography.

収録刊行物

• Tetrahedron: Asymmetry

  Tetrahedron: Asymmetry 14 (12), 1631-1636, 2003-06-20

  Elsevier

詳細情報

• CRID: 1050282676662496128
• NII論文ID: 120000872800
• NII書誌ID: AA1074621X
• ISSN: 09574166
• HANDLE: 2261/3990
• Web Site: http://hdl.handle.net/10173/724
• Web Site: https://repository.dl.itc.u-tokyo.ac.jp/records/36
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles