Commercial Scale Process of Galanthamine Hydrobromide Involving Luche Reduction: Galanthamine Process Involving Regioselective 1,2-Reduction of α,β-Unsaturated Ketone

Effect of lanthanide chloride in the Luche regioselective 1,2-reduction of 1-bromo-11-formyl-nornarwedine (5) was studied. Thus, 1-bromo-11-formyl-nornarwedine (5) is reduced with sodium borohydride in the presence of lanthanide chloride to yield 1-bromo-11-formyl-galanthamine isomers (6), which is...

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Veröffentlicht in:Organic process research & development 2013-03, Vol.17 (3), p.406-412
Hauptverfasser: Trinadhachari, Ganala Naga, Kamat, Anand Gopalkrishna, Prabahar, Koilpillai Joseph, Handa, Vijay Kumar, Srinu, Kukunuri Naga Venkata Satya, Babu, Korupolu Raghu, Sanasi, Paul Douglas
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Sprache:eng
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Zusammenfassung:Effect of lanthanide chloride in the Luche regioselective 1,2-reduction of 1-bromo-11-formyl-nornarwedine (5) was studied. Thus, 1-bromo-11-formyl-nornarwedine (5) is reduced with sodium borohydride in the presence of lanthanide chloride to yield 1-bromo-11-formyl-galanthamine isomers (6), which is a key intermediate for the commercial production of highly pure galanthamine hydrobromide (1), a modern drug against Alzheimer’s disease.
ISSN:1083-6160
1520-586X
DOI:10.1021/op300337y