Abstract
A concise and stereoselective synthesis of racemic erythro-methylphenidate ( 1 ) is described. The coupling reaction between piperidine-2-thione ( 3 ) and 2-bromo-2-phenylmethylacetate ( 4 ) afforded the β-enaminocarbonyl compound 2 in 60% yield by a modified Eschenmoser sulfide contraction reaction. In most cases the bicyclic thiazolidinone 5 was produced. Diastereoselective reduction of 2 in the presence of borohydrydes furnished the (+/−)- erythro-methylphenidate in good yields with dr >95%.
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