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A concise and stereoselective synthesis of (+/−)-erythro-methylphenidate

✍ Scribed by Dennis Russowsky; Brenno Amaro da Silveira Neto

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
121 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 b-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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