Reaktion #45102

Reaktionsgleichung

Sodium cyanoborohydride

cyclobutanone

acetic acid

tert-butyl piperazine-1-carboxylate

→

tert-butyl 4-cyclobutylpiperazine-1-carboxylate

Ausbeute 50.5%

Lösungsmittel

THF

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was evaporated to dryness
2. 2
   workup.ADDITIONmixed with water (40 mL) and 1M HCl (15 mL)
3. 3
   WaschenThe solution was washed with EtOAc (2×25 mL)
4. 4
   Extraktionextracted with EtOAc (2×15 mL)
5. 5
   WaschenThe organic layer was washed with saturated brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated

Vorschrift

Water (0.15 mL), cyclobutanone (1 g, 14.27 mmol) and acetic acid (1.742 mL, 30.44 mmol) were added to a stirred solution of tert-butyl piperazine-1-carboxylate (1.772 g, 9.51 mmol) in THF (20 mL) under nitrogen. Sodium cyanoborohydride (0.897 g, 14.27 mmol) was added portion wise over a period of 10 mins. The resulting mixture was stirred at 60° C. for 20 h. The reaction mixture was evaporated to dryness and mixed with water (40 mL) and 1M HCl (15 mL). The solution was washed with EtOAc (2×25 mL), basified with solid K2CO3 and extracted with EtOAc (2×15 mL). The organic layer was washed with saturated brine and dried over MgSO4, filtered and evaporated to afford pure tert-butyl 4-cyclobutylpiperazine-1-carboxylate (1.155 g, 50.5%) as a colourless oil.

Quelle