560132-18-5Relevant academic research and scientific papers
A concise and stereoselective synthesis of (+/-)-erythro-methylphenidate
Russowsky, Dennis,Da Silveira Neto, Brenno Amaro
, p. 2923 - 2926 (2003)
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 β-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%.
The influence of the ring size of thiolactams in the Eschenmoser coupling reaction in presence of DBU. Formation of bicyclic thiazolidinones or thioimines
Russowsky, Dennis,Da Silveira Neto, Brenno Amaro
, p. 1437 - 1440 (2007/10/03)
The different behaviors of pyrrolidin-2-thione and piperidin-2-thione under a modified Eschenmoser sulfur contraction reaction protocol using DBU as base was observed. The pyrrolidin-2-thione 1b follows the expected reaction course, leading to thioimines
