Tetrabutylammonium Fluoride → HCID 71513570, compound

HRID 2095368Notes

Reaction equation

HRID 2095368 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]#[C:22][Si](C)(C)C)[CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]#[CH:22])[CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59371759HCID 59371759, compound

Product 1

HCID 71513570HCID 71513570, compoundYield 119.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-[(trimethylsilyl)ethynyl]pyridine (500 mg, 1.3 mmol) in anhydrous THF (43 mL) was added at 0° C. 1.0M tetra-n-butylammonium fluoride solution in THF (4.0 mL, 4.0 mmol). The reaction mixture was stirred at 0° C. for 2 h. The reaction was quenched by addition of saturated aqueous NH4Cl solution. The mixture was extracted with CH2Cl2, and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by CC on SiO2 eluting with EtOAc/hexane 1:4 to give 3-[[1-(tert-butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-ethynylpyridine (470 mg, 98%).

Workup

  1. customThe reaction was quenched by addition of saturated aqueous NH4Cl solution
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by CC on SiO2 eluting with EtOAc/hexane 1:4

Sources & evidence

ORD record
ord-b7f3ba700c9e494a97857574cac5be7f
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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