Water → tert-Butyl 1-cyclopropylhydrazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

Water (24 mL) was added over 1 min to a mixture of N-nitroso-N-cyclopropyl-carbamic acid tert-butyl ester (2.01 g, 10.8 mmol), zinc powder (7.2 g, 110 mmol) and ammonium chloride (8.8 g, 165 mmol) in methanol (48 mL). An exotherm and gas evolution were noted. The mixture was stirred at room temperature for 2.25 h and at 50° C. for 2 h. The mixture was allowed to cool. It was filtered through Celite, and the Celite was washed well with methanol. The colvents were evaporated and dichloromethane (250 mL) was added. Salts were filtered off and the solution was dried (magnesium sulfate), filtered, and evaporated. The residue was passed through a cotton plug with a small amount of dichloromethane, the solvent was evaporated to give a clear oil. This was purified by chromatography using an ISCO 120 g column, eluting with 10-60% ethyl acetate/hexanes to give N-cyclopropyl-hydrazinecarboxylic acid tert-butyl ester (207 mg, 11%) as a pale yellow oil, along with a 36% yield of over-reduced cyclopropyl-carbamic acid tert-butyl ester.

Provenance & Evidence