Reaction #1688

ord-83a8bb81a8d64ea092985f3237412bba

Reaction equation

[BH4-].[Na+]
NaBH4
CC(C)(C)OC(=O)NCc1ccc([N+](=O)[O-])cc1
p-BocNHCH2C6H4NO2
[BH4-].[Na+]
NaBH4
→
CC(C)(C)OC(=O)NCc1ccc(N)cc1
white solid
Yield 97.0%
CC(C)(C)OC(=O)NCc1ccc(N)cc1
p-BocNHCH2C6H4NH2
Yield 97.0%

Reactants

[BH4-].[Na+]
NaBH4
—
NiCl2.6H2O
CC(C)(C)OC(=O)NCc1ccc([N+](=O)[O-])cc1
p-BocNHCH2C6H4NO2
[BH4-].[Na+]
NaBH4

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe solvent was evaporated in vacuo
  2. 2
    workup.DISSOLUTIONthe residue was dissolved in conc. ammonium hydroxide
  3. 3
    Extractionextracted twice with dichloromethane
  4. 4
    WashThe combined organic extracts were washed with brine
  5. 5
    Dryingdried with MgSO4
  6. 6
    Filtrationfiltered
  7. 7
    Concentrationconcentrated in vacuo

Procedure

To a stirring solution of p-BocNHCH2C6H4NO2 (7.5 g, 29.7 mmol) and NiCl2.6H2O (17.7 g, 74.3 mmol) in methanol (150 mL) at 0° C. was added NaBH4 (5.6 g, 149 mmol) in small portions over 30 min. After complete addition of NaBH4 and 15 min, the solvent was evaporated in vacuo and the residue was dissolved in conc. ammonium hydroxide and extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 6.4 g (97%) of a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726159uspto-grants-1998_03