Reaction #1909795

Reaction equation

sodium bicarbonate

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

boron tribromide

→

lasofoxifene

Yield 74.0%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   OtherThe organic layer was separated
2. 2
   Dryingdried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Procedure

To a solution of 400 mg (0.94 mmol) of cis-1-{2-[4-(6-methoxy-2-phenyl 1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy] ethyl} pyrrolidine in 25 mL of methylene chloride at 0° C. was added, dropwise with stirring, 4.7 ml (4.7 mmol) of a 1.0 M solution of boron tribromide in methylene chloride. After 3 hours at room temperature, the reaction was poured into 100 mL of rapidly stirring saturated aqueous sodium bicarbonate. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated to afford 287 mg (74% yield) of lasofoxifene as the free base.

Source