Tetrabutylammonium Fluoride Trihydrate → HCID 68640828, compound

HRID 2064526Notes

Reaction equation

HRID 2064526 reaction equation
[CH2:1]([C:8]1([N:34]([CH3:36])[CH3:35])[CH2:13][CH2:12][C:11]([CH2:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]=2[Si](CC)(CC)CC)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([CH2:17][CH2:16][CH2:15][C:11]2([OH:14])[CH2:12][CH2:13][C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([N:34]([CH3:36])[CH3:35])[CH2:9][CH2:10]2)=[CH:19]1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 68632216HCID 68632216, compound

Product 1

HCID 68640828HCID 68640828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzyl-4-dimethylamino-1-[3-(2-(triethylsilyl)-1H-indol-3-yl)propyl]cyclohexanol (2.50 g, 4.95 mmol) in anhydrous tetrahydrofuran (25 mL) was mixed with tetra-n-butyl ammonium fluoride trihydrate (6.25 g, 19.8 mmol), boiled with reflux for 7 h and then stirred overnight at room temperature. Since the conversion was not yet complete, the reaction mixture was boiled with reflux for a further 7 h and then stirred over the weekend at room temperature. The reaction mixture was concentrated to low volume in a vacuum and the residue purified by means of flash chromatography (400 g, 20×7.5 cm) with dichloromethane/methanol (95:5+1% conc. aqueous ammonia).

Workup

  1. temperaturewith reflux for 7 h
  2. temperaturewith reflux for a further 7 h
  3. stirringstirred over the weekend at room temperature
  4. concentrationThe reaction mixture was concentrated to low volume in a vacuum
  5. customthe residue purified by means of flash chromatography (400 g, 20×7.5 cm) with dichloromethane/methanol (95:5+1% conc. aqueous ammonia)

Sources & evidence

ORD record
ord-2dcf15543bb14f0eb089b9bf63ef89bb
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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