A Concise and Stereoselective Synthesis of (±)-erythro-Methylphenidate
Dennis Russowsky, and Brenno Amaro da Silveira Neto
Tetrahedron Letters, 44(14), 2923-2926 (2003) (https://www.thevespiary.org/rhodium/Rhodium/pdf/erythro-methylphenidate.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/erythro-methylphenidate.pdf)
DOI:10.1016/S0040-4039(03)00420-9 (http://dx.doi.org/10.1016/S0040%2D4039%2803%2900420%2D9)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000446159-file_n7yq.gif)
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 (https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000446159-file_feqa.gif)-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%.
Über stereoisomere 2-Piperidylphenylessigsäure-methylester
I. Weisz & A. Dudás
Monatsheft für Chemie, 840-849 (1960) (https://www.thevespiary.org/rhodium/Rhodium/pdf/methylphenidate.1960.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/methylphenidate.1960.pdf)
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Über die Darstellung von Pyridyl- und Piperidyl-aryl-acetonitrilen und einigen Umwandlungsprodukten. III Teil.
K. Scholz & L. Panizzon
Helv. Chim. Acta 37, 1605-1611 (1954) (https://www.thevespiary.org/rhodium/Rhodium/pdf/methylphenidate.1954.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/methylphenidate.1954.pdf)