반응 #1909795

ord-d5c654282e7c4be284a20e24f42097df

반응 방정식

O=C([O-])O.[Na+]
sodium bicarbonate
COc1ccc2c(c1)CC[C@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1
cis-1-{2-[4-(6-methoxy-2-phenyl 1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy] ethyl} pyrrolidine
BrB(Br)Br
boron tribromide
Oc1ccc2c(c1)CC[C@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1
lasofoxifene
수율 74.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The organic layer was separated
  2. 2
    건조dried over sodium sulfate
  3. 3
    여과filtered
  4. 4
    농축concentrated

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07037530B2uspto-grants-2006_05