Like many chiral pharmaceuticals, Ritalin, widely used to treat attention defi cit disorder, is synthesized and marketed

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Like many chiral pharmaceuticals, Ritalin, widely used to treat attention defi cit disorder, is synthesized and marketed as a racemic mixture. In 2003, a new and potentially practical synthetic route to the active enantiomer (see structure, margin) was described. The fi rst step is shown below, the reaction of dimethyl sulfate with a six-membered ring lactam. Propose a mechanism for this reaction. 

CO,CH3 'N' H Ritalin (Active stereoisomer)

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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