Reacción #3428

Ecuación de reacción

HCl

3-Bromo-3-phenylpyridine

t-BuLi

1,2,3,5,6,7-Hexahydropyrrolizinium perchlorate

→

oil

Rendimiento 14.5%

7a-(5-phenyl-3-pyridinyl)-hexahydro-1H-pyrrolizine

Rendimiento 14.5%

Disolventes

Et2O

pentane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGto stir for 30 minutes at -30° C.
2. 2
   Temperaturato warm to room temperature
3. 3
   workup.STIRRINGstir for 1 hour
4. 4
   Otrothe phases were separated
5. 5
   Extracciónextracted with CH2Cl2 (2×)
6. 6
   Secadodried (MgSO4)
7. 7
   Concentraciónconcentrated
8. 8
   Otrothe residue was chromatographed (silica gel; CHCl3 /MeOH, 95:5)

Procedimiento

3-Bromo-3-phenylpyridine (200 mg, 0.85 mmol) was dissolved in Et2O and cooled to -30° C. A solution of 2.5M t-BuLi (1.1 mL, 1.90 mmol) in pentane was added, and the reaction was stirred for 10 minutes. 1,2,3,5,6,7-Hexahydropyrrolizinium perchlorate (230 mg, 1.30 mmol) was added, and the reaction mixture was allowed to stir for 30 minutes at -30° C. then allowed to warm to room temperature and stir for 1 hour. Then 2N HCl was added, the phases were separated, and the aqueous phase was basified with 15% NaOH and extracted with CH2Cl2 (2×). The organic phases were combined, dried (MgSO4) and concentrated, and the residue was chromatographed (silica gel; CHCl3 /MeOH, 95:5) to afford a clear oil (32.5 mg).

Fuente