Water → HCID 21959538, compound

HRID 887529Notes

Reaction equation

HRID 887529 reaction equation
[CH3:1][C:2]1([CH3:25])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([C:14](=[O:24])[CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.O>CCO.[Fe]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:25])([CH3:1])[CH2:3][N:4]2[C:14](=[O:24])[CH2:15][NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 962WaterHCID 21959615HCID 21959615, compound

Product 1

HCID 21959538HCID 21959538, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1-(3,3-Dimethyl-6-nitro-2,3-dihydro-indol-1-yl)-2-(N-Boc-amino)-ethanone (3.9 g) was dissolved in EtOH (30 ml) and Fe powder (3.1 g) NH4Cl (299 mg) and H2O (5 ml) were added. The reaction was stirred at 80° C. overnight. The reaction was filtered through Celite® and evaporated off the MeOH. The residue was partitioned between CH2Cl2 and sat'd NaHCO3. The organic layer was removed, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 25% EtOAc/hexane.) The purified fractions were concentrated in vacuo to afford the compound as a white powder.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. customevaporated off the MeOH
  3. customThe residue was partitioned between CH2Cl2
  4. customThe organic layer was removed
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (SiO2, 25% EtOAc/hexane.) The purified fractions
  10. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-8b6bf0d6fdc548b8bc2760093386de30
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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