ORGN 400 |
Practical synthesis of BOC protected 2-(R)-hydroxymethylazetidine: Key intermediate for the preparation of ABT-594
| Gregory Lannoye, Global Pharmaceutical Research and Development, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064 and Jerome Menzia, Fontarome Chemical, Inc, 4170 S. Nevada Avenue, Saint Francis, WI 53235. |
| R-2-Chloro-5-(2-azetidinylmethoxy)pyridine (2) (ABT-594) was found to be a potent therapeutic agent for pain. The synthesis of ABT-594 required the development of an efficient preparation of the key building block azetidine 1. In general, few methods are known that can efficiently resolve simple azetidines. Moreover, most of the contemporary resolution methods are not amenable for large-scale preparation. Described here is a practical synthesis of diastereomeric azetidine 11 from simple starting materials and its resolution and conversion into azetidine 1 in good yield. Furthermore, the conversion of 1 into ABT-594 was achieved in several simple steps in good overall yield. 
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Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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