Reacción #2074877

Ecuación de reacción

1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen 1yl)phenoxy]ethyl]pyrrolidine hydrochloride

→

solid

Rendimiento 90.4%

cis-1-[2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1yl)phenoxy]ethyl]pyrrolidine

Rendimiento 90.4%

Disolventes

EtOH

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas hydrogenated on a Parr shaker at 50° C.
2. 2
   FiltraciónThe catalyst was filtered off with the aid of Celite
3. 3
   Otrothe solvents were removed in vacuo
4. 4
   workup.DISSOLUTIONThe resulting white solid was dissolved in CH2Cl2
5. 5
   Lavadothe solution was washed with saturated NaHCO3 (aq)
6. 6
   SecadoThe organic solution was dried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen 1yl)phenoxy]ethyl]pyrrolidine hydrochloride (nafoxidene hydrochloride) (75 g, 162 mmol) was dissolved in 1000 mL of EtOH and 300 mL of MeOH. Dry Pd(OH)2 on carbon was added and the mixture was hydrogenated on a Parr shaker at 50° C. and 50 psi (0.34 MPa) for 68 h. The catalyst was filtered off with the aid of Celite and the solvents were removed in vacuo. The resulting white solid was dissolved in CH2Cl2 and the solution was washed with saturated NaHCO3 (aq). The organic solution was dried (MgSO4), filtered, and concentrated to yield an off-white solid (62.6 g, 90%).

Fuente