(Chief Bee)
07-10-03 13:37
No 446159
      Synthesis of (±)-erythro-Methylphenidate
(Rated as: excellent)

A Concise and Stereoselective Synthesis of (±)-erythro-Methylphenidate
Dennis Russowsky,  and Brenno Amaro da Silveira Neto
Tetrahedron Letters, 44(14), 2923-2926 (2003) (../rhodium/pdf /erythro-methylphenidate.pdf)


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 -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%.
(Chief Bee)
06-03-04 18:40
No 511244
      Two Methylphenidate Syntheses
(Rated as: good read)

Über stereoisomere 2-Piperidylphenylessigsäure-methylester
I. Weisz & A. Dudás
Monatsheft für Chemie, 840-849 (1960) (../rhodium/pdf /methylphenidate.1960.pdf)
____ ___ __ _

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) (../rhodium/pdf /methylphenidate.1954.pdf)

The Hive - Clandestine Chemists Without Borders
(Hive Bee)
06-04-04 23:32
No 511512

I wonder if benzyl bromide can be substituted for
Ph-CH(Br)CO2Me in the above synthesis to yield