3-(4-Acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl ester → 3-(4-Acetoxymethylindol-3-yl)-2-amino-4-methoxy-butyric acid ethyl ester

HRID 569079Notes

Reaction equation

HRID 569079 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([N+:24]([O-])=O)[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][O:20][C:21](=[O:23])[CH3:22])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2].[H][H]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([NH2:24])[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][O:20][C:21](=[O:23])[CH3:22])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2]

Participants

5

Reactant 2

HCID 542935723-(4-Acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 539291523-(4-Acetoxymethylindol-3-yl)-2-amino-4-methoxy-butyric acid ethyl esterYield 62.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

3-(4-acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl ester (226 g) is hydrogenated in ethanol (2.3 l) with Raney nickel as catalyst under hydrogen of normal pressure without addition of heat. 3 mol of hydrogen is taken up in 31/2 hours, whereby the temperature reaches a maximum of 45° C. After filtering of the catalyst and evaporation of the residue, the raw product is chromatographed on silica gel with a mixture of dichloromethane (97.5%) and ethanol (2.5%). 130 g of the title compound as noncrystalline diastereomeric mixture is obtained.

Workup

  1. temperatureof heat
  2. custom2 hours, whereby
  3. customa maximum of 45° C
  4. filtrationAfter filtering of the catalyst and evaporation of the residue
  5. customthe raw product is chromatographed on silica gel with a mixture of dichloromethane (97.5%) and ethanol (2.5%)

Sources & evidence

ORD record
ord-ce57e382a68f4bc7b2d82dbd932c9c7a
Source dataset
uspto-grants-1988_03
Patent number
US04731365

Reaction notes

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