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

HRID 725799Notes

Reaction equation

HRID 725799 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-eae9f3d76cf94b6bbb611aadd8ed43d8
Source dataset
uspto-grants-1998_01
Patent number
US05707966

Reaction notes

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