Tetrabutylammonium Fluoride → HCID 71239417, compound

HRID 2171598Notes

Reaction equation

HRID 2171598 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[C:20]=3[CH3:28])[C@H:15]2[O:17][CH3:18])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[Cl:27][C:21]1[C:20]([CH3:28])=[C:19]([C:14]2[C@@H:15]([O:17][CH3:18])[C@@H:16]3[C@@H:9]([OH:8])[CH2:10][CH2:11][N:12]3[N:13]=2)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131732944HCID 131732944, compound

Product 1

HCID 71239417HCID 71239417, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile (400 mg, 0.954 mmol) in THF (10 mL) at 0° C. was added tetra butyl ammonium fluoride (1.9 mL, 1.909 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), reaction mixture was diluted with ethyl acetate and the organic layer was washed with water, brine, dried over Na2SO4 and concentrated to get the crude product. The product was purified by column chromatography over silica gel using 2% MeOH in DCM as solvent to provide the title compound. The absolute stereochemistry was confirmed by X-ray crystallography.

Workup

  1. custom(monitored by TLC), reaction mixture
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto get the crude product
  6. customThe product was purified by column chromatography over silica gel using 2% MeOH in DCM as solvent

Sources & evidence

ORD record
ord-2c096df7cdac4d5caab331bff83d0df1
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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