Conversion of ethyl 3-hydroxy-2-oxo-3-phenylpiperidine-1-carboxylate to 1-benzyl-2-oxo-3-phenylpiperidin-3-yl ethyl carbonate

What is the mechanism of this reaction? My proposed mechanism is shown below, would it work?

proposed mechanism

  • 2
    $\begingroup$ Sodium hydride is a non-nucleophilic base. $\endgroup$
    – Zhe
    Aug 23, 2018 at 23:46
  • $\begingroup$ Joe kent: Try forming the alkoxide with NaH first and then transfer the CO2Et group either intra- or intermolecularly. The amide ion that is left is ready for alkylation. Try it and see what you get. $\endgroup$
    – user55119
    Aug 24, 2018 at 0:25
  • $\begingroup$ Not sure the sodium hydride is intended as,a nucleophile. It could react with the benzoyl bromide. $\endgroup$ Aug 24, 2018 at 16:03

1 Answer 1


enter image description here

NaH is a strong base but a bad nucleophile. This is one possible mechanism.

  • 2
    $\begingroup$ Correct about NaH but I can’t agree with that SN2... $\endgroup$ Aug 25, 2018 at 3:20

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