Tetrabutylammonium Fluoride Trihydrate → 4-dimethylamino-4-phenyl-1-[3-(1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]-cyclohexanol

HRID 2064523Notes

Reaction equation

HRID 2064523 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]2[C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=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>[CH3:35][N:2]([CH3:1])[C:3]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]2[C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=3[NH:15][CH:14]=2)([OH:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 686297494-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]cyclohexanol

Product 1

HCID 686325804-dimethylamino-4-phenyl-1-[3-(1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]-cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]cyclohexanol (410 mg, 0.83 mmol) in anhydrous tetrahydrofuran (25 mL) was mixed with tetra-n-butyl ammonium fluoride trihydrate (1.05 g, 3.32 mmol) and boiled with reflux for 6 h. The reaction mixture was then concentrated to low volume in a vacuum and the raw product purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (2:1). The product was taken up in dichloromethane (40 mL), the solution dried with sodium sulphate and concentrated to low volume in a vacuum.

Workup

  1. temperaturewith reflux for 6 h
  2. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
  3. customthe raw product purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (2:1)
  4. dry with materialthe solution dried with sodium sulphate
  5. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-37cd72c571434f1d89a08ef68aa73dae
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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