Hydrazine → tert-butyl N-[(hydrazinecarbonyl)methyl]carbamate

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared essentially in accordance with the procedures of Tetrahedron Letters, Vol 36, No. 37 P6591-6594 as set forth herein. Under a nitrogen atmosphere in a round bottom flask, tert-butoxycarbonylamino-acetic acid methyl ester (2.0 mL, 13.5 mmol) is dissolved in absolute ethanol (50 mL) and anhydrous hydrazine (0.45 mL, 14.3 mmol) is added. The resulting mixture is heated in an oil bath at 60° C. for 3 hours then 80° C. for 5.5 hours. The reaction mixture is evaporated and the residue partitioned between water (50 mL) and dichloromethane (50 mL). The aqueous layer is extracted with dichloromethane (2×10 mL). The combined dichloromethane extracts are washed with water (2×30 mL). The dichloromethane layer is dried over magnesium sulfate and evaporated to give a solid that is triturated with diethyl ether to give hydrazinocarbonylmethyl-carbamic acid tert-butyl ester (1.94 g, 76% yield).

Provenance & Evidence