Pyridine → 3a,4,7,7a-tetrahydro-2-(((trifluoromethyl)sulfonyl)oxy)-4,7-methano-1H-isoindole-1,3(2H)-dione

HRID 743936

Reaction equation

HRID 743936 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[N:17]1[C:26](=[O:27])[CH:25]2[CH:20]([CH:21]3[CH2:28][CH:24]2[CH:23]=[CH:22]3)[C:18]1=[O:19].N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][N:17]1[C:26](=[O:27])[CH:25]2[CH:20]([CH:21]3[CH2:28][CH:24]2[CH:23]=[CH:22]3)[C:18]1=[O:19])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione

Product 1

HCID 99012903a,4,7,7a-tetrahydro-2-(((trifluoromethyl)sulfonyl)oxy)-4,7-methano-1H-isoindole-1,3(2H)-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of trifluoromethanesulfonic anhydride (6.5 g, 23 mmole) in methylene chloride (20 ml), a solution of N-hydroxy-bicyclo[2,2,1]-hept-5-ene-2,3-dicarboximide (3.6 g, 20 mmole) and pyridine (1.6 g) in methylene chloride (10 ml) was added dropwise at 0°-5° C. and continued to stir for 15 minutes at the same temperature. The reaction mixture was washed with H2O (20 ml×3), dried over anhydrous Mg SO4 and evaporated. The residue was recrystallized from ethanol to give 6.1 g of N-trifluoromethanesulfonyloxy-bicyclo[2,2,1]-hept-5-ene-2,3-dicarboximide as white needles. m.p. 89°-90° C.

Workup

  1. washThe reaction mixture was washed with H2O (20 ml×3)
  2. dry with materialdried over anhydrous Mg SO4
  3. customevaporated
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5627bca184b24259a99b7bb1017d4548
Source dataset
uspto-grants-1996_09
Patent number
US05558971

Linked notes

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