Reacción #76796

Ecuación de reacción

tetrabutylammonium fluoride

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

→

title compound

Rendimiento 59.0%

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

Rendimiento 59.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with saturated aqueous ammonium chloride solution (2 mL)
2. 2
   Extracciónextracted with ether (5×15 mL)
3. 3
   Secadodried (MgSO4)
4. 4
   Otroevaporated under reduced pressure
5. 5
   Otropurified by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol, 95:5)

Procedimiento

Under an argon atmosphere, a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.3 mL, 1.3 mmol) was added at 0° C. to a solution of (R)-(−)-5′-(2-trimethylsilylethynyl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (265 mg 0.85 mmol) in anhydrous tetrahydrofuran (5 mL), and stirred at room temperature for 2 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (2 mL), extracted with ether (5×15 mL), dried (MgSO4), evaporated under reduced pressure, and purified by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol, 95:5) to obtain the title compound (121 mg, 0.50 mmol, 59%): chemical ionization MS (m/z, relative intensity) 241 ([MH]+, 19).

Fuente