Tert-butyl (1-(4-nitrophenyl)ethyl)carbamate → tert-butyl N-[1-(4-aminophenyl)ethyl]carbamate

HRID 1779102Notes

Reaction equation

HRID 1779102 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 57219944Tert-butyl (1-(4-nitrophenyl)ethyl)carbamate

Product 1

HCID 22569414tert-butyl N-[1-(4-aminophenyl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% Pd/C (1.25 g) and tert-butyl (1-(4-nitrophenyl)ethyl)carbamate (A130) (3.78 g, 14.2 mmol) in EtOAc (50 mL) was stirred under a hydrogen atmosphere for 3 hours. The resulting solution was filtered through a pad of Celite, washing with EtOAc, then the filtrate was concentrated in vacuo to give the title compound A131 as a viscous oil (3.01 g, 89%); 1H NMR (300 MHz, CDCl3) δ 7.11 (d, J=8.1 Hz, 2H), 6.70 (d, J=8.0 Hz, 2H), 4.70 (brs, 2H), 1.44 (m, 14H). LCMS-B: 4.444 min; m/z 237 [M+H]+.

Workup

  1. filtrationThe resulting solution was filtered through a pad of Celite
  2. washwashing with EtOAc
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c071fd093e8a42fa8849b9696d85776f
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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