Reaction #41163

Reaction equation

Cyclopentanone

t-Butyl carbazate

→

N′-cyclopentyl-hydrazinecarboxylic acid tert-butyl ester

Yield 47.0%

Solvents

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled
2. 2
   Concentrationconcentrated in vacuo
3. 3
   Temperaturechilled
4. 4
   FiltrationThe crystalline material was collected by filtration

Procedure

Cyclopentanone (5.000 g, 59.44 mmol; CAS #120-92-3, purchased from Aldrich) was dissolved in hexanes (90 mL). t-Butyl carbazate (7.860 g, 59.47 mmol) was added and the mixture was heated at 65-70° C. for 1 hour. The mixture was cooled and concentrated in vacuo. The residue was taken up in isopropanol (25 mL)-ether (25 mL)-hexanes (50 mL) and chilled. The crystalline material was collected by filtration to give N′-cyclopentyl-hydrazinecarboxylic acid tert-butyl ester (5.51 g; 47%). A second crop (2.62 g, 22%) was collected from the mother liquor.

Source