Tetra-n-butylammonium tribromide → 6-(2-Bromo-acetyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

HRID 564097Notes

Reaction equation

HRID 564097 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-:21].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18](=[O:20])[CH2:19][Br:21])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 59190846Tert-butyl 6-acetyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 866236896-(2-Bromo-acetyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 1.40 g (5.09 mmol) 6-acetyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (preparation 29b) in 20 mL THF is added a solution of 2.45 g (5.09 mmol) tetrabutylammonium-tribromide in MeOH/THF at RT. The reaction mixture is stirred 30 min at RT and the solvent is evaporated. The residue is treated with water and 1 M aqueous HCl-solution and the aqueous phase is extracted with tert-butylmethylether. The organic phase is washed with water and 1 M aqueous HCl-solution, dried over MgSO4, filtered and the solvent is evaporated. The residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent.

Workup

  1. customthe solvent is evaporated
  2. additionThe residue is treated with water and 1 M aqueous HCl-solution
  3. extractionthe aqueous phase is extracted with tert-butylmethylether
  4. washThe organic phase is washed with water and 1 M aqueous HCl-solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. customThe residue is purified by silica gel column chromatography with PE/EtOAc (7:3) as eluent

Sources & evidence

ORD record
ord-201f5fefdf28489d8a17fa8c2ed2a77c
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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