Triethylamine → 2-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dione

HRID 720773Notes

Reaction equation

HRID 720773 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]([CH3:21])[CH:8]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH3:9].C(N(CC)CC)C>CCOCC>[CH3:9][CH:8]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 600337Phthalimide, N-(2-hydroxy-3-butyl)-

Product 1

HCID 218952722-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dioneYield 82.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methanesulfonyl chloride (9.7 mL, 56 mmol) was added to a solution of 10.5 g (48 mmol) of 2-(2-hydroxy-1-methylpropyl)-1H-isoindole-1,3(2H)-dione (JP 01242569 A2) and 8.1 mL (58 mmol) of triethylamine and the mixture was stirred at room temperature overnight. The mixture was diluted with ether and washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which slowly solidified. Trituration with hexanes gave 11.8 g of 2-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-1H-isoindole-1,3(2H)-dione as a white solid, mp 67–73° C.

Workup

  1. washwashed with water and brine
  2. customDrying
  3. custom(MgSO4) and removal of solvent
  4. customgave an oil which

Sources & evidence

ORD record
ord-95d5b461c8a34a4b83e574550293ea2e
Source dataset
uspto-grants-2006_11
Patent number
US07135585B2

Reaction notes

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