Tert-butyl 2-tert-butyl-5-nitrobenzylcarbamate → Tert-butyl 2-tert-butyl-5-aminobenzylcarbamate

HRID 74072Notes

Reaction equation

HRID 74072 reaction equation
[C:1]([C:5]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:6]=1[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O.CO.[Pd]>[C:1]([C:5]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:6]=1[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 57470261Tert-butyl 2-tert-butyl-5-nitrobenzylcarbamate

Product 1

HCID 57470262Tert-butyl 2-tert-butyl-5-aminobenzylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of tert-butyl 2-tert-butyl-5-nitrobenzylcarbamate (20 mg, 0.065 mmol) in 5% AcOH-MeOH (1 mL) was added 10% Pd—C (14 mg) under nitrogen atmosphere. The mixture was stirred under H2 (1 atm) at room temperature for 1 h. The catalyst was removed via filtration through Celite, and the filtrate was concentrated to give tert-butyl 2-tert-butyl-5-aminobenzylcarbamate (E-4), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.09 (d, J=8.5 Hz, 1H), 6.62 (d, J=2.6 Hz, 1H), 6.47 (dd, J=8.5, 2.6 Hz, 1H), 4.61 (br s, 1H), 4.40 (d, J=5.1 Hz, 2H), 4.15 (br s, 2H), 1.39 (s, 9H), 1.29 (s, 9H); HPLC ret. time 2.47 min, 10-100% CH3CN, 5 min gradient; ESI-MS 279.3 m/z (MH+).

Workup

  1. customThe catalyst was removed via filtration through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ece4a6dc8bde472d9adcd7d305ccd85b
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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