Ammonium formate → Tert-Butyl (2-(4-aminophenyl)-2-methylpropyl)carbamate

HRID 74086Notes

Reaction equation

HRID 74086 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:12][C:2]([C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)([CH3:1])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22981239Tert-butyl 2-methyl-2-(4-nitrophenyl)propylcarbamate

Product 1

HCID 22981167Tert-Butyl (2-(4-aminophenyl)-2-methylpropyl)carbamateYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a refluxing solution of tert-butyl 2-methyl-2-(4-nitrophenyl)propylcarbamate (725 mg, 2.5 mmol) and ammonium formate (700 mg, 10.9 mmol) in EtOH (25 mL) was added Pd-5% wt on carbon (400 mg). The mixture was refluxed for 1 h, cooled and filtered through Celite. The filtrate was concentrated to give tert-butyl 2-methyl-2-(4-aminophenyl)propylcarbamate (G-3) (550 mg, 83%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 6.99 (d, J=8.5 Hz, 2H), 6.49 (d, J=8.6 Hz, 2H), 4.85 (s, 2H), 3.01 (d, J=6.3 Hz, 2H), 1.36 (s, 9H), 1.12 (s, 6H); HPLC ret. time 2.02 min, 10-99% CH3CN, 5 min run; ESI-MS 265.2 m/z (MH+).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-66c255cb1a994ac391e1ddac99714dc3
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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