1h-Indole-1-carboxylic acid,2,3-dihydro-7-methyl-4-nitro-,1,1-dimethylethyl ester → 1-t-Butoxycarbonyl-4-amino-2,3-dihydro-7-methylindole

HRID 1275669Notes

Reaction equation

HRID 1275669 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([N+:18]([O-])=O)[CH:13]=[CH:14][C:15]=2[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([NH2:18])[CH:13]=[CH:14][C:15]=2[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 158963761h-Indole-1-carboxylic acid,2,3-dihydro-7-methyl-4-nitro-,1,1-dimethylethyl ester

Product 1

HCID 224612391-t-Butoxycarbonyl-4-amino-2,3-dihydro-7-methylindoleYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-t-Butoxycarbonyl-2,3-dihydro-7-methyl-4-nitroindole (2.169 g; 8.7 mmol) is dissolved in methanol (35 mL), treated with a catalytic amount of 10% palladium-on-carbon (210 mg) and placed under an atmosphere of hydrogen. The solution is allowed to stir overnight. The black suspension is filtered through Celite and the solvent is removed by rotary evaporation. The crude product is purified by silica gel flash column chromatography using 15% ethyl acetate/hexanes as eluent to afford 1.769 g of 1-t-butoxycarbonyl-4-amino-2,3-dihydro-7-methylindole as a white solid (94% yield).

Workup

  1. filtrationThe black suspension is filtered through Celite
  2. customthe solvent is removed by rotary evaporation
  3. customThe crude product is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-5d848112ee544f36b027162e9b222cbc
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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