| Journal: | Revista de la Sociedad Química de México |
| Database: | PERIÓDICA |
| System number: | 000190967 |
| ISSN: | 0583-7693 |
| Authors: | García, Cirilo1 Tapia, Josefina Cervantes, Humberto |
| Institutions: | 1Universidad Autónoma Metropolitana, Departamento de Ciencias Básicas, México, Distrito Federal. México |
| Year: | 2002 |
| Season: | Ene-Mar |
| Volumen: | 46 |
| Number: | 1 |
| Pages: | 49-53 |
| Country: | México |
| Language: | Inglés |
| Document type: | Artículo |
| Approach: | Experimental |
| Spanish abstract | El presente estudio describe la transformación del ácido 3β-acetoxi-23,24-dinorcol-5-en-22-oico al (20S)-3β-acetoxi-23,24-dinorcol-5-en-22-aldehido. La transformación se realizó a través de la (20S)-22-(1H-imidazol-1-il)-3β-acetoxi-23,24-dinorcol-5-en-22-ona, cuya reducción con hidruro de tri-t-butoxialuminio-litio dio el aldehido mencionado arriba y el acetato de 22-hidroxi-23,24-dinorcol-5-en-3β-ilo, el imidazólido sin reaccionar y el ácido esteroidal de partida. La posibilidad de reciclar el ácido esteroidal y el imidazólido, y de oxidar el acetato de 22-hidroxi-23,24-dinorcol-5-en-3β-ilo al producto objetivo, son las características distintivas del presente método. Se incluye una breve discusión del análisis estructural de los productos intermediarios y finales, y acerca de la estabilidad del imidazólido y del aldehido deseado |
| English abstract | Commercial 3β-acetoxy-23,24-dinorchol-5-en-22-oic acid was transformed into (20S)-3β-acetoxy-23,24-dinorchol-5-en-22-aldehyde in a two-step process. The key step was reduction of the imidazolide derived from the above mentioned acid, which invariably produced the target aldehyde and 22-hydroxy-23,24-dinorchol-5-en-3β-yl acetate. In adittion to these products, the work-up of the organic material from the latter reaction, afforded pregn-5-en-3β-yl acetate along with the mixture of the former acid and its unreacted imidazolide. Oxidation of 22-hydroxy-23,24-dinorchol-5-en-3β-yl acetate with pyridinium chlorochromate and recycling of the mixture acid/imidazolide, enhances the practical value of this process. Structural analysis, based on 1H NMR spectroscopy and polarimetry of intermediate and final products, and observations on the stability of the imidazolyl derivative and aldehyde are briefly discussed |
| Disciplines: | Química |
| Keyword: | Química orgánica, Acidos, Aldehídos, Síntesis |
| Keyword: | Chemistry, Organic chemistry, Acids, Aldehydes, Synthesis |
| Full text: | Texto completo (Ver PDF) |
