Triethylamine → N'-(2-ethoxy-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.00 g, 6.8 mmol), 2-ethoxyphenylboronic acid (Combiblock; 1.12 g, 6.8 mmol), copper(II) acetate (1.24 g, 6.8 mmol) and triethylamine (960 μL, 6.8 mmol) in 1,2-dichloroethane (15 mL) was heated in an oil bath at 50° C. overnight. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 120 g column, eluting with 20-25% ethyl acetate/hexanes, to give N′-(2-ethoxy-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (751 mg, 38%) as an off-white solid.

Provenance & Evidence