01240nas a2200289 4500008004100000022001400041245005300055210005300108260000800161300001200169490000600181520040000187653002900587653001400616653002200630653001200652653001600664100002000680700001700700700002700717700002400744700002500768700002500793700002400818700002400842856008400866 2020 eng d a2193-580700aHighly enantioselective synthesis of sitagliptin0 aHighly enantioselective synthesis of sitagliptin cFEB a189-1910 v93 a
A highly enantioselective synthesis of sitagliptin, a potent DPP-4 inhibitor, is reported. Explicitly identified chiral FerroLANE ligands in the presence of rhodium catalyze the asymmetric hydrogenation of an enamine to yield sitagliptin with excellent enantioselectivity (98% ee). The process was scaled up to 5 g and the final product was isolated as a phosphate salt with >99% ee.
10aasymmetric hydrogenation10acatalysis10aFerroLANE ligands10aRhodium10asitagliptin1 aKhopade, Kishor1 aSen, Anirban1 aBirajdar, Rajkumar, S.1 aPaulbudhe, Uday, P.1 aKavale, Dattatry, S.1 aShinde, Prashant, S.1 aMhaske, Santosh, B.1 aChikkali, Samir, H. uhttp://library.ncl.res.in/content/highly-enantioselective-synthesis-sitagliptin