Hydrogenation of a Chiral 1H-Benz[de]isoquinolin-1-one and an Equilibration Using Palladium Catalyst
| Autor: | Bruce A. Kowalczyk and, Norman H. Dyson |
|---|---|
| Rok vydání: | 1997 |
| Předmět: |
chemistry.chemical_classification
Hydrochloride Organic Chemistry Palonosetron Diastereomer Salt (chemistry) Palonosetron Hydrochloride Photochemistry Catalysis chemistry.chemical_compound chemistry Palladium on carbon medicine Organic chemistry Physical and Theoretical Chemistry Palladium catalyst medicine.drug |
| Zdroj: | Organic Process Research & Development. 1:117-120 |
| ISSN: | 1520-586X 1083-6160 |
| DOI: | 10.1021/op970201w |
| Popis: | The catalytic hydrogenation of a chiral 1H-benz[de]isoquinolin-1-one to palonosetron and the undesired diastereomer was optimized using a variety of conditions and catalysts. The most selective catalyst for the production of palonosetron was an unreduced palladium on carbon catalyst. The (+)- and (−)-camphorsulfonic acid salts of the 1H-benz[de]isoquinolin-1-one and the complex of the 1H-benz[de]isoquinolin-1-one with Mg2+ upon catalytic hydrogenation gave the greatest preference for the undesired diastereomer. An equilibration of the undesired diastereomer from hydrogenation and palonosetron as hydrochloride salts using hydrogen-activated palladium on carbon catalyst under a nitrogen atmosphere was developed. The procedure was used to recycle the hydrochloride salt of the undesired diastereomer from hydrogenation into pure palonosetron hydrochloride. |
| Databáze: | OpenAIRE |
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