Cyclopentanone → tert-Butyl 2-Cyclopentylhydrazinecarboxylate
Reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[NH:8][NH2:9]>>[C:12]([O:11][C:7]([NH:8][NH:9][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]Participants
3
Conditions
- Temperature
- 67.5 °C
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.