Synthesis and conformational study of some diastereoisomeric 4-methyl-3-phenyl-3-piperidinols and related esters

Add time:08/27/2019    Source:sciencedirect.com

Diastereoisomeric 4-methyl-3-phenyl-3-piperidinols and related esters have been prepared by phenylation of 4-methyl-3-piperidones and subsequent acylation. The synthesis of the intermediate piperidones is also described. Configurational and conformational assignments are based on the IR and NMR study of OH absorption bands of the diastereoisomeric pair II, of the desmethyl analogue X (R = H) and of VII. NMR spectroscopic differences found in the ester Me group, as affected by magnetic anisotropy of the C-3-Ph substituent, also provide useful guidance in the assignment of configurations and probable conformations.

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