4-Hydroxy-1-methyl-4-phenylpiperidine is quaternised by ethyl bromoacetate to give 55 ± 2% of the isomer formed by equatorial approach. The orientations of the products formed were proved by the lactonisation (of the boat form) of that isomer which has an axial N-methyl group in the usual chair form.
H. Dorn, A. R. Katritzky and M. R. Nesbit, J. Chem. Soc. B, 1967, 501 DOI: 10.1039/J29670000501
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