Reacción #987944

Ecuación de reacción

N-methoxy-N-methylcycloheptanecarboxamide

3-lithiopyridine

→

cycloheptyl(3-pyridinyl)methanone

Cycloheptyl(3-pyridinyl)methanone

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by addition of aqueous saturated NH4Cl
2. 2
   Temperaturato warm to room temperature
3. 3
   workup.ADDITIONdiluted with ether
4. 4
   OtroThe layers were separated
5. 5
   Extracciónthe aqueous phase was extracted 3 times with ether
6. 6
   LavadoCombined organic layers were washed with brine
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated
9. 9
   OtroAfter purification by chromatography on silica gel (CH2Cl2)

Procedimiento

A solution of N-methoxy-N-methylcycloheptanecarboxamide (1.11 g, 6 mmol) in ether (10 ml) was added dropwise at −78° C. to a solution of 3-lithiopyridine (prepared by addition of BuLi (3.75 ml, 6 mmol) to 3-bromopyridine (0.58 ml, 6 mmol) in ether (25 ml) at −78° C.). The mixture was stirred for 2 hours at −78° C., quenched by addition of aqueous saturated NH4Cl, allowed to warm to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted 3 times with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (CH2Cl2), the cycloheptyl(3-pyridinyl)methanone 18 was obtained as a slightly yellow oil (490 mg, 40%).

Fuente