I recently conducted a reductive amination between methyl pyruvate and benzylamine using sodium triacetoxyborohydride to yield N-benzylalanine methyl ester (IUPAC: (S)-methyl 2-(benzylamino)propanoate). Any thoughts on its acidity or basicity? The pH meter I have isn't functioning and a prediction will help. Thank you very much. enter image description here

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    $\begingroup$ Basic enough to form a salt with a strong acid. You will need a mildy basic aq workup if you want to be sure of it extracting into organic phase. $\endgroup$
    – Waylander
    Sep 22 at 13:13
  • $\begingroup$ It is unclear to me why you mention IUPAC: (S)-methyl 2-(benzylamino)propanoate when the product is clearly going to be racemic according to the reaction conditions you describe. $\endgroup$
    – user55119
    Sep 22 at 16:24


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