Hydrogen Bromide → Lasofoxifene

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence