Tetrahydrofuran → Benzyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 412529Notes

Reaction equation

HRID 412529 reaction equation
Br.[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.O1CCCC1.[C:18](Cl)(=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[OH-].[Na+]>[CH2:20]([O:19][C:18]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=2)[CH2:10]1)=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 112184631,2,3,4-tetrahydroisoquinolin-7-ol Hydrobromide

Product 1

HCID 11254587Benzyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 89.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

7-Hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (3 g) was dissolved in 1N aqueous sodium hydroxide solution (46 ml) and tetrahydrofuran (10 ml) and benzyl chlorocarbonate (2.45 g) was added. The mixture was stirred at room temperature for 30 min. The reaction mixture was extracted with chloroform and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was dried under reduced pressure to give the title compound (3.3 g).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-48582dae7b8341a28d9fd21d277e6c31
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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