Reacción #720604

Ecuación de reacción

tert-butyl (3S,4S)-4-(2-chloro-4-nitrophenoxy)-3-fluoropiperidine-1-carboxylate

NH4Cl

→

desired product

Rendimiento 45.0%

tert-butyl (3S,4S)-4-(4-amino-2-chlorophenoxy)-3-fluoropiperidine-1-carboxylate

Rendimiento 45.0%

Disolventes

EtOAc

EtOH H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to room temperature
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   Otroto leave a crude solid
4. 4
   Otropartitioned with H2O (50 mL)
5. 5
   OtroOrganic layers were separated
6. 6
   Lavadothe aqueous layer was washed with EtOAc (50 mL)
7. 7
   SecadoThe combined organic layers were dried over Na2SO4
8. 8
   Concentraciónconcentrated under vacuum

Procedimiento

A mixture of tert-butyl (3S,4S)-4-(2-chloro-4-nitrophenoxy)-3-fluoropiperidine-1-carboxylate (0.8 g, 1.0 eq, 2.2 mmol), Fe (0.6 g, 5.0 eq, 10.8 mmol) and NH4Cl (0.6 g, 5.0 eq, 10.8 mmol) in EtOH/H2O (1:1, 50 mL) was stirred at 90° C. for 1 hour. The mixture was cooled to room temperature and concentrated under reduced pressure to leave a crude solid. The crude mixture was dissolved in EtOAc (50 mL) and partitioned with H2O (50 mL). Organic layers were separated and the aqueous layer was washed with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum to give the desired product in 45% yield. This product was taken to next step with out further purification.

Fuente