Sodium borohydride → HCID 66743119, compound

HRID 449722Notes

Reaction equation

HRID 449722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:17])([CH3:16])[CH:14]=[O:15])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86662325HCID 86662325, compound

Product 1

HCID 66743119HCID 66743119, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(8-Fluoro-1-oxo-1,2-dihydroisoquinolin-6-yl)-2-methylpropanal (137 mg, 587 μmol) was dissolved in MeOH and cooled in an ice bath. To the resulting solution was added NaBH4 (33 mg, 881 μmol) in one portion. The reaction mixture was stirred vigorously for 5 minutes before removing the cooling bath and stirring for 30 minutes. To the reaction mixture was added about 40 ml of 10% HCl and 40 ml EtOAc. The mixture was shaken and the EtOAc phase collected. The organic phase was washed with an equal volume of water. The aqueous phase was back extracted with 2×30 ml EtOAc. The combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to afford 109 mg of a off-white powder. (M+H)+=236 m/e.

Workup

  1. temperaturecooled in an ice bath
  2. custombefore removing the cooling bath
  3. stirringstirring for 30 minutes
  4. additionTo the reaction mixture was added about 40 ml of 10% HCl and 40 ml EtOAc
  5. stirringThe mixture was shaken
  6. customthe EtOAc phase collected
  7. washThe organic phase was washed with an equal volume of water
  8. extractionThe aqueous phase was back extracted with 2×30 ml EtOAc
  9. dry with materialThe combined organic phase was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-982520fc462e4f1c92a53bb0f25f1c34
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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