Tetrabutylammonium Fluoride Trihydrate → (R)-1-(3-(1H-indol-3-yl)-2-methylpropyl)-4-(dimethylamino)-4-phenylcyclohexanol

HRID 2064537Notes

Reaction equation

HRID 2064537 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][C@H:11]([CH3:29])[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>[NH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([CH2:12][C@@H:11]([CH3:29])[CH2:10][C:6]2([OH:9])[CH2:7][CH2:8][C:3]([N:2]([CH3:36])[CH3:1])([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:4][CH2:5]2)=[CH:14]1

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 68629968(R)-4-dimethylamino-1-[2-methyl-3-(2-(triethylsilyl)-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

Product 1

HCID 68640809(R)-1-(3-(1H-indol-3-yl)-2-methylpropyl)-4-(dimethylamino)-4-phenylcyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-4-dimethylamino-1-[2-methyl-3-(2-(triethylsilyl)-1H-indol-3-yl)propyl]-4-phenylcyclohexanol (175 mg, 0.34 mmol) in anhydrous tetrahydrofuran (30 mL) was mixed with tetra-n-butyl ammonium fluoride trihydrate (109 mg, 0.34 mmol) and stirred for 4 h with reflux. The reaction mixture was then concentrated to low volume in a vacuum and the residue was purified by flash chromatography (10 g, 20×1.5 cm) with ethyl acetate/methanol (95:5).

Workup

  1. temperaturewith reflux
  2. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
  3. customthe residue was purified by flash chromatography (10 g, 20×1.5 cm) with ethyl acetate/methanol (95:5)

Sources & evidence

ORD record
ord-00dbd0cf759643558347381e09639b33
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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