Triethylamine → (S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol

HRID 45992Notes

Reaction equation

HRID 45992 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([S:28](Cl)(=[O:30])=[O:29])=[C:23]([CH3:32])[CH:22]=1>ClCCl>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH3:32])[C:24]([S:28]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][C@H:2]2[CH2:10][OH:11])(=[O:29])=[O:30])=[C:25]([CH3:27])[CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6951186(S)-(+)-2-IndolinemethanolHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 57989609(S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanolYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cold (0° C.) solution of (S)-indolin-2-ylmethanol (4.60 mmol, 1.2 equiv.) and triethylamine (2.5 equiv.) in dichloromethane (20 ml) was added dropwise 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (3.83 mmol, 1.0 equiv.) in dichloromethane (5 ml) and the reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane, washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography. Yield: 72%.

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22a154f28b114d2ea8d063a8e694a9b1
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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