Ethanol → HCID 24257677, compound

HRID 2383057Notes

Reaction equation

HRID 2383057 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][N:9](C(=O)C(F)(F)F)[CH:10]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCO>C1COCC1>[CH3:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][NH:9][CH:10]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 59396614HCID 59396614, compound

Product 1

HCID 24257677HCID 24257677, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (900 mg) was added to a mixed solution of a solution of 5,8-dimethoxy-1-phenyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (4.21 g) in THF (30 mL), and EtOH (100 mL) at room temperature under stirring. The reaction mixture was stirred at room temperature for 3 hours and then stirred at 40° C. for 30 minutes, and concentrated under reduced pressure. To the resulting residue was added a 3 M aqueous HCl solution (30 mL), followed by refluxing for 5 minutes. After cooling, the mixture was made strong alkaline by using a 20% aqueous NaOH solution and extracted with chloroform. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 5,8-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (3.05 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. stirringstirred at 40° C. for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. additionTo the resulting residue was added a 3 M aqueous HCl solution (30 mL)
  5. temperatureby refluxing for 5 minutes
  6. temperatureAfter cooling
  7. extractionextracted with chloroform
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cff970c56c14b5eb21f89c4095cbe5c
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

Loading…