Ethyl Acetate → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-hydroxyethyl-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369096Notes

Reaction equation

HRID 1369096 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:20]([F:23])([F:22])[F:21])[CH:11]=[C:12](C(OCC)=O)[CH:13]=2)[C:8]([OH:34])([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[C:7]1=[O:35])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C([O-])(O)=O.[Na+].[C:53](OCC)(=[O:55])[CH3:54]>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:36][CH3:37])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:20]([F:21])([F:23])[F:22])[CH:11]=[C:12]([CH2:54][CH2:53][OH:55])[CH:13]=2)[C:8]([OH:34])([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)[C:7]1=[O:35])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 185186261-(2-Diethylaminoethyl)-4-trifluoromethyl-6-ethoxycarbonyl-3-hydroxy-3-(2-naphthyl)oxindoleHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 185185581-(2-Diethylaminoethyl)-4-trifluoromethyl-6-hydroxyethyl-3-hydroxy-3-(2-naphthyl)oxindoleYield 9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-ethoxycarbonyl-3-hydroxy-3-(2-naphthyl)oxindole (605 mg, 0. 118 mmol) in toluene (1 mL) was added dropwise 1.01 N diisobutylaluminium hydride in toluene (0.36 mL, 0.364 mmol). The mixture was allowed to warm to room temperature over 4 h. Sat. aqueous NaHCO3 and ethyl acetate were added. Insoluble materials were removed by filtration and the organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography with 30:1 to 15:1 chloroform/methanol to give the title compound (5 mg, 9%).

Workup

  1. customInsoluble materials were removed by filtration
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 30:1 to 15:1 chloroform/methanol

Sources & evidence

ORD record
ord-6891bc95f20b46618c71b5fbe4a28de5
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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