Trifluoromethanesulfonic anhydride → HCID 22132527, compound

HRID 1856783Notes

Reaction equation

HRID 1856783 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[C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH2:29][CH2:30][N:31]3[C:35](=[O:36])[C:34]4=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]4[C:32]3=[O:41])[CH2:24]2)=[CH:19][CH:18]=1>N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[C:32]1(=[O:41])[N:31]([CH2:30][CH2:29][CH2:28][CH2:27][N:23]2[CH2:22][CH2:21][C:20]3[C:25](=[CH:26][C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:18][CH:19]=3)[CH2:24]2)[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]12

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 22132507HCID 22132507, compound

Product 1

HCID 22132527HCID 22132527, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.53 ml, 3.14 mmol) was added dropwise with stirring to an ice-cooled solution of 7-hydroxy-2-(4-phthalimidobutyl)-1,2,3,4-tetrahydroisoquinoline (1 g, 2.86 mmol) in anhydrous pyridine (10 ml). After stirring at room temperature for 18 h the reaction mixture was added to 10% aqueous Copper (II) sulfate (100 ml) and extracted into ethyl acetate (200 ml). The organic layer was separated, washed with 10% aqueous copper (II) sulfate (2×50 ml), dried (Na2SO4) and evaporated in vacuo. Chromatography on silica gel using 10-100% ethyl acetate-hexane gradient elution gave the title compound as a green oil (0.45 g, 33%).

Workup

  1. extractionextracted into ethyl acetate (200 ml)
  2. customThe organic layer was separated
  3. washwashed with 10% aqueous copper (II) sulfate (2×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. washChromatography on silica gel using 10-100% ethyl acetate-hexane gradient elution

Sources & evidence

ORD record
ord-10e07c1c25644260af08968804dbcce3
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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