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Volumn 38, Issue 1, 2009, Pages 100-101

Synthesis of melatonin receptor agonist Ramelteon via Rh-eatalyzed asymmetric hydrogenation of an allylamine

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EID: 67650474163     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.100     Document Type: Article
Times cited : (20)

References (27)
  • 19
    • 67650489596 scopus 로고    scopus 로고
    • Chem Abstr. 1999, 131, 44725.
    • (1999) Chem Abstr , vol.131 , pp. 44725
  • 20
    • 67650501518 scopus 로고    scopus 로고
    • Experiments were carried out under argon atmosphere by standard Schlenk techniques (Table 1, Entry 11, To a solution of, 2E, 2-(1, 2, 6, 7-tetrahydro-8H-indeno[5, 4-b]furan-8-ylidene) ethyl]amine (1, 20 mg, 0.1 mmol) in methanol (0.5 mL) in a glass autoclave was added a solution of (R)-11, S, 2-(di-2-furylphosphino) ferrocenyl]ethyldi (tert-butyl) phosphine (ligand 3k, 2.7 mg, 1.3 equiv to Rh) and [Rh (cod) Cl]2 (1.0 mg, s/c=25) in methanol (0.5 mL) by cannula. Hydrogen (0.7 MPa) was introduced, and the reaction mixture was stirred at room temperature. After 5 h, enantiomeric excess (92, and chemical yield (95, were determined by HPLC analysis (CHIRALCEL OD-RH, eluted with 0.1 M KPF6 (pH 2) /acetonitrile=750/250 v/v, 0.5 mL/rnin
    • 6 (pH 2) /acetonitrile=750/250 (v/v), 0.5 mL/rnin).


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