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Rhodium (Chief Bee) 07-10-03 13:37 No 446159 |
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Synthesis of (±)-erythro-Methylphenidate (Rated as: excellent) |
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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.rhodium.ws/pdf/erythro-meth DOI:10.1016/S0040-4039(03)00420-9 [image] 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 [image]-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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Rhodium (Chief Bee) 06-03-04 18:40 No 511244 |
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Two Methylphenidate Syntheses (Rated as: good read) |
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Über stereoisomere 2-Piperidylphenylessigsäure-methylester I. Weisz & A. Dudás Monatsheft für Chemie, 840-849 (1960) (https://www.rhodium.ws/pdf/methylphenid ____ ___ __ _ 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.rhodium.ws/pdf/methylphenid The Hive - Clandestine Chemists Without Borders |
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cattleprodder (Hive Bee) 06-04-04 23:32 No 511512 |
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2-benzylpiperidine | ||||||
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I wonder if benzyl bromide can be substituted for Ph-CH(Br)CO2Me in the above synthesis to yield 2-benzylpiperidine. |
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