Réaction #52052

Équation de réaction

Diethyl azodicarboxylate

PPh3

2-Benzylamino-cyclohexanol

→

crude product

Rendement 75.0%

7-Benzyl-7-Azabicyclo[4.1.0]heptane

Rendement 75.0%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter addition
2. 2
   Autrethe ice bath was removed
3. 3
   workup.STIRRINGthe mixture stirred at room temperature for 36 h
4. 4
   FiltrationThe resulting crystalline precipitate was filtered
5. 5
   Autrethe solvent removed from the filtrate by rotary evaporation

Mode opératoire

Cyclization of 2-Benzylamino-cyclohexanol. Diethyl azodicarboxylate (Aldrich, 95%, 3.6 ml, 22.6 mmol) was slowly added to an ether solution (50 ml) of 2-benzylaminio-cyclohexanol (3.1 g, 15 mmol) and PPh3 (5.94 g, 22.6 mmol) under N2, with stirring, in an ice-bath. After addition, the ice bath was removed, and the mixture stirred at room temperature for 36 h. The resulting crystalline precipitate was filtered and the solvent removed from the filtrate by rotary evaporation to yield the crude product, which was purified by column chromatography (petroleum ether: diethyl ether=50:50) (2.1 g, 75% yield).

Source