Water → 6-methoxy-2,3-dihydro-1H-indole

HRID 1790440Notes

Reaction equation

FC1C=CC(CCN2CCC([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[CH:16]=[CH:15]3)CC2)=CC=1.O>FC(F)(F)C(O)=O>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][CH2:15][NH:14]2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 1 M solution (0.18 ml) of a borane/tetrahydrofuran complex was added dropwise at 0° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxyindole (24 mg) in trifluoroacetic acid (1 ml) over 2 min followed by stirring at 0° C. for 30 min. Af ter the completion of the reaction, water (0.1 ml) was added thereto and the resulting reaction solution was concentrated under reduced pressure. The resulting residue was dissolved in a 2 N aqueous solution of sodium hydroxide and stirred at room temperature for 10 min. The mixture was extracted with methylene chloride. The organic layer was separated and dried over magnesium sulfate. After concentrating the solvent under reduced pressure, the resulting residue was purified by preparative TLC to give 1-[1-(4-fluorophenethyl)piperidin-4-yl)]-6-methoxyindoline (10 mg) (yield: 35%).

Workup

additionwas added
customthe resulting reaction solution
concentrationwas concentrated under reduced pressure
dissolutionThe resulting residue was dissolved in a 2 N aqueous solution of sodium hydroxide
stirringstirred at room temperature for 10 min
extractionThe mixture was extracted with methylene chloride
customThe organic layer was separated
dry with materialdried over magnesium sulfate
concentrationAfter concentrating the solvent under reduced pressure
customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record: ord-a3024f37927f46e597f945009b3e32ef
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071201B2

Reaction notes

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