Reaction #1909797

Reaction equation

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

HBr

→

cis-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalene-2-ol

Solvents

acetic acid

Conditions

Workup

1. 1
   TemperatureThe solution was cooled
2. 2
   Filtrationthe resulting white precipitate was collected by filtration
3. 3
   workup.DISSOLUTIONThe hydrobromide salt (9.6 g, 69%) was dissolved in CHCl3/MeOH
4. 4
   OtherThe layers were separated
5. 5
   Extractionthe aqueous layer was further extracted with CHCl3/MeOH
6. 6
   DryingThe combined organic layers were dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   Otherto yield product as an off-white foam

Procedure

A mixture of cis-1-[2-[4-(6-methoxy-2-phenyl-1,2,3,4 tetrahydronaphthalen-1-yl)phenoxy] ethyl}pyrrolidine (12 g, 28 mmol), acetic acid (75 mL), and 48% HBr (75 mL) was heated at 100° C. for 15 h. The solution was cooled and the resulting white precipitate was collected by filtration. The hydrobromide salt (9.6 g, 69%) was dissolved in CHCl3/MeOH and was stirred with saturated NaHCO3 (aq). The layers were separated and the aqueous layer was further extracted with CHCl3/MeOH. The combined organic layers were dried (MgSO4), filtered, and concentrated to yield product as an off-white foam.

Source