Réaction #1909795

Équation de réaction

sodium bicarbonate

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

boron tribromide

→

lasofoxifene

Rendement 74.0%

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer was separated
2. 2
   Séchagedried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Mode opératoire

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