반응 #76792

반응 방정식

(S)-(+)-5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

styrene

triethylamine

→

title compound

수율 55.0%

(S)-(+)-5′-(E)-(Phenylethenyl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

수율 55.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타was purged with argon
2. 2
   기타sealed with a Teflon plug and FETFE O-ring
3. 3
   온도cooled to room temperature
4. 4
   workup.DISSOLUTIONdissolved in chloroform (10 mL)
5. 5
   세척washed with saturated aqueous sodium carbonate (1 mL)
6. 6
   건조dried (MgSO4)
7. 7
   기타evaporated under reduced pressure
8. 8
   기타Recrystallization from ethyl acetate

실험 절차

A solution of (S)-(+)-5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (150 mg, 0.51 mmol), styrene (0.07 mL, 0.61 mmol), palladium(II)acetate (1.2 mg, 0.0053 mmol), tri-o-tolylphosphine (6.4 mg, 0.021 mmol), and triethylamine (0.5 mL, 3.6 mmol) in anhydrous acetonitrile (0.5 mL), in a heavy-walled threaded glass tube containing a magnetic stir bar, was purged with argon and sealed with a Teflon plug and FETFE O-ring. The mixture was stirred and heated at 100° C. for 2 hours, cooled to room temperature, dissolved in chloroform (10 mL), washed with saturated aqueous sodium carbonate (1 mL), dried (MgSO4), and evaporated under reduced pressure. Recrystallization from ethyl acetate afforded the title compound (90 mg, 0.28 mmol, 55%) as a light tan solid: electrospray MS (m/z, relative intensity) 319 ([MH]+, 100).

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