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

Temperature

60 °C

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).

1. customThe title compound was prepared essentially in accordance with the procedures of Tetrahedron Letters, Vol 36
2. customThe reaction mixture is evaporated
3. customthe residue partitioned between water (50 mL) and dichloromethane (50 mL)
4. extractionThe aqueous layer is extracted with dichloromethane (2×10 mL)
5. washThe combined dichloromethane extracts are washed with water (2×30 mL)
6. dry with materialThe dichloromethane layer is dried over magnesium sulfate
7. customevaporated
8. customto give a solid
9. customthat is triturated with diethyl ether

ORD record

ord-b920737c74e84495a6a518b0640b1a66

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173682B2