4-Toluenesulfonyl chloride → N-(4-methylbenzenesulfonyl)-octahydroisoindole-1-carboxylic acid

HRID 23884Notes

Reaction equation

HRID 23884 reaction equation
[CH:1]1([C:10]([OH:12])=[O:11])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][NH:2]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:2]2[CH2:3][CH:4]3[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:1]2[C:10]([OH:12])=[O:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 13207250octahydro-1H-isoindole-1-carboxylic acid

Product 1

HCID 22569248N-(4-methylbenzenesulfonyl)-octahydroisoindole-1-carboxylic acidYield 62.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Octahydroisoindole-1-carboxylic acid (0.125 g; 0.74 mmol) from Example 1, Step A, p-toluenesulfonyl chloride (0.155 g; 0.814 mmol), and sodium carbonate (0.157 g; 1.48 mmol) were dissolved in water (3 mL). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and washed with EtOAc. The water layer was acidified with concentrated. HCl and extracted with CH2Cl2 (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford N-(4-methylbenzenesulfonyl)-octahydroisoindole-1-carboxylic acid (0.15 g).

Workup

  1. washwashed with EtOAc
  2. concentrationwith concentrated
  3. extractionHCl and extracted with CH2Cl2 (2×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82d1effbf97645f3b2657ef9d0779921
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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