Water → 1-[1-(4-Fluorophenethyl)piperdin-4-yl]-6-(1-hydroxyethyl)indoline

HRID 1790453Notes

Reaction equation

HRID 1790453 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([C:25](=[O:27])[CH3:26])[CH:23]=4)[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(OCC)(=O)C.O>C(O)C>[F:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([CH:25]([OH:27])[CH3:26])[CH:23]=4)[CH2:18][CH2:17]3)[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 220381171-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetylindoline

Product 1

HCID 220378991-[1-(4-Fluorophenethyl)piperdin-4-yl]-6-(1-hydroxyethyl)indolineYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.03 g) was added to a solution (5 ml) of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetylindoline (0.17 g) in ethanol and the resultant mixture was stirred at room temperature overnight. Then ethyl acetate and water were added to the reaction solution and the layers were separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Then the residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (150 mg) as a colorless oil (yield: 89%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen the residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-5934a8dc59a344e399a8ff0010ae2aa2
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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