Tetrahydrofuran → (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.O1CCCC1.C[Si](C)(C)[C:26]#[C:27][C:28]1[CH:29]=[C:30]2[CH2:36][C@:35]3([CH:41]4[CH2:42][CH2:43][N:38]([CH2:39][CH2:40]4)[CH2:37]3)[O:34][C:31]2=[N:32][CH:33]=1>>[C:27]([C:28]1[CH:29]=[C:30]2[CH2:36][C@:35]3([CH:41]4[CH2:40][CH2:39][N:38]([CH2:43][CH2:42]4)[CH2:37]3)[O:34][C:31]2=[N:32][CH:33]=1)#[CH:26]Participants
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 tetrahydofouran (5×15 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-1de5ffec36e34488bcbb55a8692145e0
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706878B2
Reaction notes
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