Reaction #1909796

Reaction equation

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

→

solid

Yield 90.4%

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

Yield 90.4%

Solvents

EtOH

MeOH

Conditions

Workup

1. 1
   Otherwas hydrogenated on a Parr shaker at 50° C.
2. 2
   FiltrationThe catalyst was filtered off with the aid of Celite
3. 3
   Otherthe solvents were removed in vacuo
4. 4
   workup.DISSOLUTIONThe resulting white solid was dissolved in CH2Cl2
5. 5
   Washthe solution was washed with saturated NaHCO3 (aq)
6. 6
   DryingThe organic solution was dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

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%).

Source