tert-Butyl (3-{[(2-fluoro-4-nitrophenyl)carbonyl](methyl)amino}propyl)methylcarbamate → tert-Butyl (3-{[(4-amino-2-fluorophenyl)carbonyl](methyl)amino}propyl)methylcarbamate

HRID 446514Notes

Reaction equation

HRID 446514 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]([N:13]([CH3:26])[CH2:14][CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:12].[H][H]>CO.[C].[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]([N:13]([CH3:26])[CH2:14][CH2:15][CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:12])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 86663428tert-Butyl (3-{[(2-fluoro-4-nitrophenyl)carbonyl](methyl)amino}propyl)methylcarbamateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86663429tert-Butyl (3-{[(4-amino-2-fluorophenyl)carbonyl](methyl)amino}propyl)methylcarbamateYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of the compound (300 mg, 0.810 mmol) obtained in Example 12a in methanol (8 mL) was added to 10% palladium-carbon (dry; 30 mg), the atmosphere in the system was replaced with a hydrogen atmosphere, and then the mixture was stirred at room temperature for 30 minutes. The atmosphere in the system was replaced with a nitrogen atmosphere, then 10% palladium-carbon (dry; 90 mg) was further added, the atmosphere in the system was replaced with a hydrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. The atmosphere in the system was replaced with a nitrogen atmosphere, and then the mixture was filtered through celite. The solvent was evaporated under reduced pressure to give the title compound (260 mg; yield, 95%) as a light brown oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. filtrationthe mixture was filtered through celite
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-366f45b8d13345d5b47c808e72686a7f
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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