반응 #76795

반응 방정식

(R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

trimethylsilylacetylene

triethylamine

→

title compound

수율 90.0%

(R)-(−)-5′-(2-Trimethylsilylethynyl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

수율 90.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.ADDITIONcontaining a magnetic stir bar
2. 2
   기타purged with argon
3. 3
   기타sealed with a Teflon plug and FETFE O-ring
4. 4
   온도cooled to room temperature
5. 5
   workup.DISSOLUTIONdissolved in chloroform (25 mL)
6. 6
   세척washed with saturated aqueous sodium carbonate (2 mL)
7. 7
   건조dried (MgSO4)
8. 8
   기타evaporated under reduced pressure
9. 9
   기타Purification by flash chromatography through silica gel (eluting with ammoniated ether/methanol, 9:1)

실험 절차

(R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine](295 mg, 1 mmol), trimethylsilylacetylene (0.355 mL, 2.5 mmol), tetrakis(triphenylphosphine)palladium (230 mg, 0.2 mmol), triethylamine (2 mL) and anhydrous acetonitrile (2 mL) were combined in a heavy-walled threaded glass tube containing a magnetic stir bar, purged with argon and sealed with a Teflon plug and FETFE O-ring. The mixture was stirred and heated at 100° C. for 4 hours, cooled to room temperature, dissolved in chloroform (25 mL), washed with saturated aqueous sodium carbonate (2 mL), dried (MgSO4), and evaporated under reduced pressure. Purification by flash chromatography through silica gel (eluting with ammoniated ether/methanol, 9:1) afforded the title compound (280 mg, 0.90 mmol, 90%): chemical ionization MS (m/z, relative intensity) 313 ([MH]+, 30).

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