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

HRID 1592Notes

Reaction equation

HRID 1592 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[BH4-].[Na+]>CO>[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 10610803tert-Butyl 4-nitrobenzylcarbamate

Product 1

HCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in conc. ammonium hydroxide
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83a8bb81a8d64ea092985f3237412bba
Source dataset
uspto-grants-1998_03
Patent number
US05726159

Reaction notes

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