Convenient preparations of di-t-butyl and methyl t-butyl iminodicarboxylates. The use of methyl t-butyl iminodicarboxylate potassium salt as a modified Gabriel reagent
Abstract
The oxidation of t-butyl oxamate in the presence of t-butyl alcohol or methanol is a convenient means of preparing di-t-butyl and methyl t-butyl iminodicarboxylate respectively. The latter forms a crystalline, stable, non-hygroscopic potassium salt. The salt undergoes smooth N-alkylation in dipolar aprotic solvents, except with alkylating agents which are susceptible to base catalysed side reactions. The fully substituted derivatives produced give N-t-butoxycarbonylamino compounds on mild treatment with alkali, thus permitting the direct conversion R–X → R–NH Boc.
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