Réaction #1688

Équation de réaction

NaBH4

p-BocNHCH2C6H4NO2

NaBH4

→

white solid

Rendement 97.0%

p-BocNHCH2C6H4NH2

Rendement 97.0%

Solvants

methanol

Conditions de réaction

Traitement

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

Mode opératoire

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