Triethylamine → HCID 57941318, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.50 g, 10.26 mmol), 2-naphthaleneboronic acid (Lancaster; 1.90 g, 11.05 mmol), copper(II) acetate (1.90 g, 10.46 mmol) and triethylamine (3.6 mL, 25.8 mmol) in 1,2-dichloroethane (40 mL) was heated in an oil bath at 50° C. for 45 min. 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 15-20% ethyl acetate/hexanes, to give N-methyl-N′-naphthalen-2-yl-hydrazinecarboxylic acid tert-butyl ester (1.26 g, 45%) as an orange oil that partially solidified. The Boc region of the 1H NMR spectrum integrated high, but the material was used directly in subsequent steps without further purification.

Provenance & Evidence