Sodium Hydroxide → 5-Ethyl-1-(phenylsulfonyl)indoline

HRID 1529644Notes

Reaction equation

HRID 1529644 reaction equation
[BH4-].[Na+].[C:3]1([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21](=O)[CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)(C(F)(F)F)=O.O>[C:3]1([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 141129561-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone

Product 1

HCID 141129525-Ethyl-1-(phenylsulfonyl)indolineYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
25 °C

Procedure

To magnetically stirred TFA (1600 mL) was added at 0° C. sodium borohydride (64 g, 1.69 mol) over 1 h. To this mixture was added dropwise a solution of 1-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanone (40 g, 0.13 mol) in TFA (700 mL) over 1 h. The mixture was stirred overnight at 25° C., diluted with H2O (1600 ml), and basified with sodium hydroxide pellets at 0° C. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 1-benzenesulfonyl-5-ethyl-2,3-dihydro-1H-indole (16.2 g, 43%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-75d377b354734e3580c7b90086a8aa3f
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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