Tetrabutylammonium Fluoride → (R)-(-)-5'-Ethynylspiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si](C)(C)[C:21]#[C:22][C:23]1[CH:24]=[C:25]2[CH2:31][C@:30]3([CH:36]4[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]4)[CH2:32]3)[O:29][C:26]2=[N:27][CH:28]=1>O1CCCC1>[C:22]([C:23]1[CH:24]=[C:25]2[CH2:31][C@:30]3([CH:36]4[CH2:35][CH2:34][N:33]([CH2:38][CH2:37]4)[CH2:32]3)[O:29][C:26]2=[N:27][CH:28]=1)#[CH:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- customThe reaction was quenched with saturated aqueous ammonium chloride solution (2 mL)
- extractionextracted with ether (5×15 mL)
- dry with materialdried (MgSO4)
- customevaporated under reduced pressure
- custompurified by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol, 95:5)
Sources & evidence
- ORD record
- ord-f443ec689b664f709bab6334af3f7375
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06703502B2
Reaction notes
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