(+/-)-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester → (+/-)-2-amino-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-propionic acid methyl ester

HRID 41055Notes

Reaction equation

HRID 41055 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([CH3:21])([N+:18]([O-])=O)[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH3:17])[CH:13]=2)[NH:8][CH:7]=1>CO>[CH3:1][O:2][C:3](=[O:22])[C:4]([NH2:18])([CH3:21])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:16][CH3:17])[CH:13]=2)[NH:8][CH:7]=1

Participants

3

Reactant 1

HCID 86634329(+/-)-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester

Product 1

HCID 68851521(+/-)-2-amino-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-propionic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (+/−)-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester (5.3 g, 17.3 mmol) in dry methanol (50 ml) Raney nickel 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, 95:5) to give (+/−)-2-amino-3-(5-ethoxy-1H-indol-3-yl)-2-methyl-propionic acid methyl ester (4.2 g, 90%) as a white crystals. M.p. 165-166° C. (from ethyl acetate-hexane).

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, 95:5)

Sources & evidence

ORD record
ord-512f4907283b4e5f8a469848b2c4ebb9
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

Loading…