(+/-)-3-[5-(2-methoxy-ethoxy)-1H-indol-3-yl]-2-methyl-2-nitro-propionic acid methyl ester → HCID 68853029, compound

HRID 41056Notes

Reaction equation

HRID 41056 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]([CH3:23])([N+:20]([O-])=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:13]=2)[NH:8][CH:7]=1>CO>[CH3:1][O:2][C:3](=[O:24])[C:4]([NH2:20])([CH3:23])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:13]=2)[NH:8][CH:7]=1

Participants

3

Reactant 1

HCID 86634330(+/-)-3-[5-(2-methoxy-ethoxy)-1H-indol-3-yl]-2-methyl-2-nitro-propionic acid methyl ester

Product 1

HCID 68853029HCID 68853029, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (+/−)-3-[5-(2-methoxy-ethoxy)-1H-indol-3-yl]-2-methyl-2-nitro-propionic acid methyl ester (12.7 g, 37.8 mmol) in dry methanol (200 ml) Raney nickel (ca 20 g) is added and the mixture is stirred at room temperature under H2 at atmospheric pressure overnight. The reaction mixture is filtered through a pad of Celite and the solid is washed with methanol. The filtrate is concentrated and the residue is purified by column chromatography (dichloromethane-methanol, 9:1) to give (+/−)-2-amino-3-[5-(2-methoxy-ethoxy)-1H-indol-3-yl]-2-methyl-propionic acid methyl ester (5.98 g, 52%). M.p. 117-118 (from ethyl acetate-light petroleum).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of Celite
  2. washthe solid is washed with methanol
  3. concentrationThe filtrate is concentrated
  4. customthe residue is purified by column chromatography (dichloromethane-methanol, 9:1)

Sources & evidence

ORD record
ord-21729ef35f2044dfb39aa201f03c92e8
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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