Reacción #68674

Ecuación de reacción

3-bromo-8-chloro-1,5-naphthyridine

butyllithium

tert-butyl 4-oxopiperidine-1-carboxylate

→

tert-butyl 4-(8-chloro-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate

Rendimiento 38.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with saturated NH4Cl
2. 2
   Extracciónextracted with dichloromethane (3×20 mL)
3. 3
   Secadodried over NaSO4
4. 4
   Concentraciónconcentrated
5. 5
   OtroIntermediate was purified via MPLC (DCM/MeOH/NHOH)

Procedimiento

Dissolved 3-bromo-8-chloro-1,5-naphthyridine (210 mg, 862 μmol) in 8 mL of THF and cooled to −78° C. Then added butyllithium (517 μl, 1294 μmol) and stirred for 15 min. Added tert-butyl 4-oxopiperidine-1-carboxylate (258 mg, 1294 μmol) and let warm to room temperature over 1 h. The reaction was quenched with saturated NH4Cl and extracted with dichloromethane (3×20 mL), dried over NaSO4 and concentrated. Intermediate was purified via MPLC (DCM/MeOH/NHOH) to yield tert-butyl 4-(8-chloro-1,5-naphthyridin-3-yl)-4-hydroxypiperidine-1-carboxylate (120 mg, 38% yield.

Fuente