Process research and development of an NK-1 receptor antagonist. Enantioselective trifluoromethyl addition to a ketone in the preparation of a chiral isochroman

…, NM Do, JE Sieser, P Arpin, E Vazquez

文献索引：Caron, Stephane; Do, Nga M.; Sieser, Janice E.; Arpin, Patrice; Vazquez, Enrique Organic Process Research and Development, 2007 , vol. 11, # 6 p. 1015 - 1024

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被引用次数: 41

摘要

CJ-17,493 (4) is a chiral NK-1 receptor antagonist. It was first prepared through a diastereoselective crystallization, then through chiral chromatography of a key intermediate, and ultimately via asymmetric synthesis. Multiple routes for the preparation of a key isochroman were demonstrated, and conditions for improved regioselectivity of a Friedel– Crafts acylation were identified. Cesium fluoride was found to be an acceptable initiator for ...