Sodium borohydride → tert-butyl N-[(4-aminophenyl)methyl]carbamate

Participants

Reaction Steps

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.

Provenance & Evidence