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

HRID 2064517Notes

Reaction equation

HRID 2064517 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:21]3[C:16](=[CH:17][CH:18]=[CH:19][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>[CH3:35][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:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)([OH:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 689168264-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-indol-3-yl)propyl]cyclohexanol

Product 1

HCID 686302084-dimethylamino-1-[3-(1H-indol-3-yl)propyl]-4-phenylcyclohexanolYield 11.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-indol-3-yl)propyl]cyclohexanol (852 mg, 1.8 mmol) in absolute tetrahydrofuran (50 mL) was mixed with tetra-n-butyl ammonium fluoride trihydrate (1.66 g, 5.3 mmol), stirred 6 h with reflux, then stirred over the weekend at 50° C. and then concentrated to low volume in a vacuum. The residue was purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (9:1). 80 mg of the title compound were obtained that were stirred overnight with cyclohexane (20 mL). 406 mg of the target compound were also obtained, which contained still larger amounts of impurity. This mixture was purified once again by flash chromatography (38 g, 20×2.5 cm), in which case cyclohexane/ethyl acetate (4:1) was firstly used as mobile solvent. All fractions that contained the target compound were treated with cyclohexane as above.

Workup

  1. temperaturewith reflux
  2. stirringstirred over the weekend at 50° C.
  3. concentrationconcentrated to low volume in a vacuum
  4. customThe residue was purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-97a5d466d6ae40f385c2603b7502e91b
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

Loading…