861064-70-2Relevant articles and documents
Functionalization of Piperidine Derivatives for the Site-Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate
Babl, Tobias,Davies, Huw M. L.,Liu, Wenbin,R?ther, Alexander,Reiser, Oliver
supporting information, (2020/03/23)
Rhodium-catalyzed C?H insertions and cyclopropanations of donor/acceptor carbenes have been used for the synthesis of positional analogues of methylphenidate. The site selectivity is controlled by the catalyst and the amine protecting group. C?H functionalization of N-Boc-piperidine using Rh2(R-TCPTAD)4, or N-brosyl-piperidine using Rh2(R-TPPTTL)4 generated 2-substitited analogues. In contrast, when N-α-oxoarylacetyl-piperidines were used in combination with Rh2(S-2-Cl-5-BrTPCP)4, the C?H functionalization produced 4-susbstiuted analogues. Finally, the 3-substituted analogues were prepared indirectly by cyclopropanation of N-Boc-tetrahydropyridine followed by reductive regio- and stereoselective ring-opening of the cyclopropanes.