Dichloromethane → 1-Oxo-1,2,3,4-tetrahydroisoquinolin-6-YL trifluoromethanesulfonate

HRID 389101Notes

Reaction equation

HRID 389101 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3](Cl)(=[O:5])=[O:4].[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[NH:15][CH2:14][CH2:13]2.C(N(CC)CC)C.ClCCl>O>[F:1][C:2]([F:8])([F:7])[S:3]([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[NH:15][CH2:14][CH2:13]2)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 534141981-Oxo-1,2,3,4-tetrahydroisoquinolin-6-YL trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoromethanesulfonyl chloride (1.0 ml) was added dropwise to a mixture of 6-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (1.52 g), triethylamine (1.3 ml) and dichloromethane (5 ml), followed by stirring at room temperature for 2 hours. Water was added to the reaction solution, followed by extraction with chloroform, the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 50:50), and the solvent was evaporated under reduced pressure to obtain, as a colorless powdery solid, 1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl trifluoromethanesulfonate (1.56 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 50:50)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-03994ab8bec94e2fbf3744389b597846
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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