Reacción #48315

Ecuación de reacción

4-azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline

water

THF

triphenylphosphine

→

desired product

6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinolin-4-amine

Disolventes

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was heated to 40 deg C
2. 2
   workup.ADDITIONfunnel containing 0.5 MHCl
3. 3
   LavadoThe aqueous layer was washed 5×DCM
4. 4
   Lavadowashed 3× with EtOAc
5. 5
   Secadodried with MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated

Procedimiento

To a solution of 4-azido-6-bromo-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (2.29 g, 8.15 mmol), water (6.50 ml, 361 mmol), and THF (20.4 ml, 8.15 mmol) was added triphenylphosphine (2.35 g, 8.96 mmol) in one portion. The resulting mixture was heated to 40 deg C. and stirred overnight. The crude mixture was dissolved with EtOAc and transferred to a sep. funnel containing 0.5 MHCl. The aqueous layer was washed 5×DCM. The aqueous layer was then neutralized with 6N NaOH and washed 3× with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to provide the desired product. MS m/z: 239 (M−NH2).

Fuente