Reacción #1528418

Ecuación de reacción

tert-butyl 4-cyanopiperidine-1-carboxylate

2-(chloromethyl)pyridine

potassium bis(trimethylsilyl)amide

→

desired product

Tert-butyl 4-cyano-4-(pyridine-2-ylmethyl)piperidine-1-carboxylate

Disolventes

toluene

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in an ice bath
2. 2
   Extracciónextracted with EtOAc (3×30 ml)
3. 3
   LavadoThe combined organic extracts were washed with brine (30 ml)
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   Otroto give a orange oil
8. 8
   OtroThe crude product was chromatographed on silica
9. 9
   Lavadoeluted with 50% EtOAc in isohexane

Procedimiento

To a stirred suspension of tert-butyl 4-cyanopiperidine-1-carboxylate (500 mg; 2.38 mmol) and 2-(chloromethyl)pyridine (334 mg; 2.62 mmol) in toluene (3.6 ml) cooled in an ice bath was added a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene; 5.7 ml; 2.86 mmol) over 10 minutes. The reaction mixture was allowed to warm to ambient temperature with stirring for 1.5 hours. The reaction was poured into brine (25 ml) and extracted with EtOAc (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried over MgSO4, filtered and evaporated to give a orange oil. The crude product was chromatographed on silica eluted with 50% EtOAc in isohexane to give the desired product a colourless oil. (375 mg)

Fuente