tert-butyl 5-nitro-2,3-dihydro-1H-inden-2-ylcarbamate → tert-butyl N-(5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

HRID 1814774Notes

Reaction equation

HRID 1814774 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54019012tert-butyl 5-nitro-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 42609144tert-butyl N-(5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (5-nitro-indan-2-yl)-carbamic acid tert-butyl ester (3.52 g, 12.6 mmol) in ethanol (100 mL) is degassed and 10% palladium on carbon added. The reaction is evacuated and placed under 1 atm H2(g) for 2 h. Filtration of the reaction mixture through Celite is followed by concentration of the filtrate under reduced pressure to give (5-amino-indan-2-yl)-carbamic acid tert-butyl ester as an oil which is used directly without further purification.

Workup

  1. customThe reaction is evacuated
  2. filtrationFiltration of the reaction mixture through Celite

Sources & evidence

ORD record
ord-eb4ee049d4f947beade1c3d186cbee08
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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