Takemoto, Toshiyasu published the artcileAsymmetric synthesis of enantiomerically pure spiro [((2S)-hydroxy)indane-1,4′-piperidine], Quality Control of 137419-24-0, the main research area is spirohydroxyindanepiperidine enantioselective preparation intermediate tachykinin receptor antagonist; asym synthesis enantiomerically pure spirohydroxyindanepiperidine.
Two methods for the preparation of enantiomerically pure spirohydroxyindanepiperidine (S)-I (R = H), a key intermediate for the synthesis of a tachykinin receptor antagonist, from indenepiperidine II (R = H) are described. E.g., II (R = Me3COCO, Boc) was epoxidized with methyltrioxorhenium, the epoxide opened regioselectively to the 2-indanone derivative which was oxidized with PCC and then reduced enantioselectively in the presence of an Corey-Bakshi-Shibata oxazaborolidine catalyst to give N-Boc (S)-I (R = Boc) in 100% yield and 89% ee from the 2-indanone derivative E.g., II (R = Boc) was epoxidized enantioselectively with the (R,R)-Jacobsen epoxidation catalyst to give epoxide III in 51% yield and 91% ee; III was reduced regioselectively with ammonium formate in the presence of palladium on carbon, and the Boc derivative was then deprotected with HCl in dioxane to give the hydrochloride salt of I (R = H).
Tetrahedron: Asymmetry published new progress about Epoxidation, stereoselective. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Quality Control of 137419-24-0.
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem