Reaktion #41163

ord-a55d876453f4475cb4c8243c9b31c485

Reaktionsgleichung

O=C1CCCC1
Cyclopentanone
CC(C)(C)OC(=O)NN
t-Butyl carbazate
CC(C)(C)OC(=O)NNC1CCCC1
N′-cyclopentyl-hydrazinecarboxylic acid tert-butyl ester
Ausbeute 47.0%

Reagenzien

Keine

Lösungsmittel

Reaktionsbedingungen

Temperatur
67.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture was cooled
  2. 2
    Einengenconcentrated in vacuo
  3. 3
    Temperaturchilled
  4. 4
    FiltrationThe crystalline material was collected by filtration

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728029B2uspto-grants-2010_06