Tetrabutylammonium Fluoride → HCID 71239141, compound

HRID 2171600Notes

Reaction equation

HRID 2171600 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([Cl:32])[C:25]=3[CH3:33])[C@H:15]2[O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[Cl:32][C:26]1[C:25]([CH3:33])=[C:24]([C:14]2[C@@H:15]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)[C@@H:16]3[C@@H:9]([OH:8])[CH2:10][CH2:11][N:12]3[N:13]=2)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131732945HCID 131732945, compound

Product 1

HCID 71239141HCID 71239141, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-(tetrahydro-2H-pyran-2-yloxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile (120 mg, 0.245 mmol) in THF (2 mL) at 0° C. was added tetrabutylammonium fluoride (0.49 mL, 0.490 mmol, 1M solution in THF) and the reaction mixture was stirred at room temperature for 3 h. Once the starting material had disappeared (monitored by TLC), it was diluted with ethyl acetate and the organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification of crude by column chromatography over silica gel using 30% EtOAc in hexane provided the title compound.

Workup

  1. washthe organic layer was washed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification of crude by column chromatography over silica gel using 30% EtOAc in hexane

Sources & evidence

ORD record
ord-346c47f84ffa4c2bb51e24fcf2f4f3dd
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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