An Efficient Scalable Route for the Synthesis of Enantiomerically Pure tert-Butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
| العنوان: | An Efficient Scalable Route for the Synthesis of Enantiomerically Pure tert-Butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate |
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| المؤلفون: | William Maton, Fernando Bravo, Paolo Stabile, Daniele Andreotti, Arnaldo Nalin, Simone Spada, Roberto Profeta, Alcide Perboni, Federica Stazi, Damiano Castoldi, Anna Mingardi, Stefano Provera, Emanuele Miserazzi, Nicola Giubellina, Mario Mattioli, Roberta Pachera, Pieter Westerduin, Arianna Ribecai, Simon M. Bryant, Lucilla Turco, Angelo M. Manzo |
| المصدر: | Organic Process Research & Development. 14:1239-1247 |
| بيانات النشر: | American Chemical Society (ACS), 2010. |
| سنة النشر: | 2010 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Heptane, Organic Chemistry, Diastereomer, chemistry.chemical_compound, Hydrolysis, chemistry, Yield (chemistry), Organic chemistry, Epimer, Hydroxymethyl, Carboxylate, Physical and Theoretical Chemistry, Lactone |
| الوصف: | An efficient scalable route to synthesize the enantiomerically pure tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate is described. Compared to the original routes, significant improvements were made by using an innovative approach starting from commercially available chiral lactone. In this approach, one of the key steps described is an elegant epimerization/hydrolysis of the undesired diastereoisomer avoiding tedious purification. The chemistry has been scaled up to produce kilogram amounts of tert-butyl-(1R,4S,6R)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate in 43% yield over nine chemical transformations. |
| تدمد: | 1520-586X 1083-6160 |
| DOI: | 10.1021/op100164v |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::cb19119ea9299a9302fec3bb306f634d https://doi.org/10.1021/op100164v |
| رقم الانضمام: | edsair.doi...........cb19119ea9299a9302fec3bb306f634d |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 1520586X 10836160 |
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| DOI: | 10.1021/op100164v |