Tetrabutylammonium Fluoride Trihydrate → 4-dimethylamino-1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

HRID 2064520Notes

Reaction equation

HRID 2064520 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][C:14]=2[Si](CC)(CC)CC)([OH:9])[CH2:5][CH2:4]1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:36][N:2]([CH3:1])[C:3]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][CH:14]=2)([OH:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 689182644-dimethylamino-1-[3-(5-fluoro-2-triethylsilanyl-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

Product 1

HCID 689159774-dimethylamino-1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-dimethylamino-1-[3-(5-fluoro-2-triethylsilanyl-1H-indol-3-yl)propyl]-4-phenylcyclohexanol (350 mg, 0.69 mmol) in absolute tetrahydrofuran (25 mL) was mixed with tetra-n-butyl ammonium fluoride trihydrate (868 mg, 2.8 mmol)), stirred 6 h with reflux, then stirred overnight at room temperature. The reaction mixture was then concentrated to low volume in a vacuum and the residue was purified by means of flash chromatography (18 g, 20×2.0 cm) with ethyl acetate/methanol (9:1).

Workup

  1. temperaturewith reflux
  2. stirringstirred overnight at room temperature
  3. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
  4. customthe residue was purified by means of flash chromatography (18 g, 20×2.0 cm) with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-15ff4ccad6c7418dbdd4825f9e29d553
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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