Tetrabutylammonium Fluoride → (R)-3'-(4-Bromofuran-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:21]=[C:22]([N:29]2[CH2:33][C@:32]3([CH:38]4[CH2:39][CH2:40][N:35]([CH2:36][CH2:37]4)[CH2:34]3)[O:31][C:30]2=[O:41])[O:23][C:24]=1[Si](C)(C)C>O1CCCC1>[Br:19][C:20]1[CH:21]=[C:22]([N:29]2[CH2:33][C@:32]3([CH:38]4[CH2:37][CH2:36][N:35]([CH2:40][CH2:39]4)[CH2:34]3)[O:31][C:30]2=[O:41])[O:23][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Tetra-n-butylammonium fluoride (1M solution in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added to a solution of (R)-3′-[4-bromo-5-(trimethylsilyl)furan-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (577 mg, 1.44 mmol) in tetrahydrofuran (5 mL). The solution was heated at 70° C. (bath temperature) for 6 h. The reaction mixture was evaporated to dryness, and the residue was subjected to flash chromatography using a gradient of ammoniated methanol in chloroform as the eluant give the title compound as a pale brown solid (387 mg), m/z 327, 329 (MH+).
Workup
- customThe reaction mixture was evaporated to dryness
Sources & evidence
- ORD record
- ord-a99725dcb8db40e0afcb66eac8c922ec
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514567B2
Reaction notes
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