Benzenesulfonyl chloride → 1-(benzenesulfonyl)-octahydro-1H-indole-2-carboxylic acid

HRID 650034Notes

Reaction equation

HRID 650034 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:11]1[CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:13][CH:12]1[C:20]([OH:22])=[O:21]>[OH-].[Na+]>[C:1]1([S:7]([N:11]2[CH:19]3[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:13][CH:12]2[C:20]([OH:22])=[O:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 3274680Octahydroindole-2-carboxylic acid

Product 1

HCID 217141261-(benzenesulfonyl)-octahydro-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

29.8 mmol (3.8 ml) of benzenesulphonyl chloride and 7.4 ml of 4M sodium hydroxide solution are added in succession to a solution, cooled to 0° C., of 29.6 mmol (5 g) of 2-perhydroindolecarboxylic acid in 7.4 ml of 4M NaOH. The reaction mixture is left at room temperature, with stirring, for 24 hours. The mixture is then rendered acidic to pH 2-3 and filtered. The resulting solid is washed with ether to yield the expected product.

Workup

  1. waitThe reaction mixture is left at room temperature
  2. filtrationrendered acidic to pH 2-3 and filtered
  3. washThe resulting solid is washed with ether

Sources & evidence

ORD record
ord-f669244576054fe181f75fff73fd0550
Source dataset
uspto-grants-2001_08
Patent number
US06271247B1

Reaction notes

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