Tetrabutylammonium Fluoride → HCID 86714071, compound

HRID 576379Notes

Reaction equation

HRID 576379 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26][Si](C(C)C)(C(C)C)C(C)C)=[C:21]([CH:37]([C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[O:38][Si](C(C)C)(C(C)C)C(C)C)[CH:20]=2)[O:7][C@@H:6]1[CH2:57][O:58][C:59](=[O:61])[CH3:60])(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[C:21]([CH:37]([C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[OH:38])[CH:20]=2)[O:7][C@@H:6]1[CH2:57][O:58][C:59](=[O:61])[CH3:60])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86714072HCID 86714072, compound

Product 1

HCID 86714071HCID 86714071, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 4) To a solution of compound 149 (870 mg, 0.98 mmol) in tetrahydrofuran (10.0 mL) was slowly added tetrabutylammonium fluoride solution (5.0 mL, 1.0M in tetrahydrofuran) at 0° C. and the reaction mixture was stirred for 2 h. The resulting mixture was quenched with sat. NH4Cl solution, diluted with EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude was purified by silica gel column chromatography to provide (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-((4-ethylphenyl)(hydroxy)methyl)-4-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (150, 500 mg, 89%) as a pale yellow solid.

Workup

  1. customat 0° C.
  2. customThe resulting mixture was quenched with sat. NH4Cl solution
  3. additiondiluted with EtOAc
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc156cc170b649908b20e983618f1358
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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