Synthesis of (±)-erythro-Methylphenidate

[Rhodium]

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)
DOI:

10.1016/S0040-4039(03)00420-9

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000446159-file_n7yq.gif" title="View this 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 https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000446159-file_feqa.gif" title="View this 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%.

[Rhodium]

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)
____ ___ __ _

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)

[cattleprodder]

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