Реакция #76796

Уравнение реакции

tetrabutylammonium fluoride

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

→

title compound

Выход 59.0%

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

Выход 59.0%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was quenched with saturated aqueous ammonium chloride solution (2 mL)
2. 2
   Экстракцияextracted with ether (5×15 mL)
3. 3
   Сушкаdried (MgSO4)
4. 4
   Другоеevaporated under reduced pressure
5. 5
   Другоеpurified by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol, 95:5)

Методика

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).

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