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

Access this Article

Search this Article

Abstract

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.

Journal

  • Tetrahedron: Asymmetry

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

    Elsevier

Codes

  • NII Article ID (NAID)
    120003308694
  • NII NACSIS-CAT ID (NCID)
    AA1074621X
  • Text Lang
    ENG
  • Article Type
    journal article
  • ISSN
    0957-4166
  • Data Source
    IR 
Page Top