5-Methoxy-N,N-dimethyl-1H-indole-3-methanamine → (+/-)-3-(5-methoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester

HRID 41057

Reaktionsgleichung

Reaktionsgleichung von HRID 41057
CN([CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[N+:16]([CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])([O-:18])=[O:17]>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:23][O:22][C:20](=[O:21])[C:19]([CH3:24])([N+:16]([O-:18])=[O:17])[CH2:4][C:5]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([O:14][CH3:15])[CH:10]=2)[NH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 279655-Methoxy-N,N-dimethyl-1H-indole-3-methanamineHCID 547818Methyl 2-nitropropanoate

Produkt 1

HCID 58212093(+/-)-3-(5-methoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl esterAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of commercially available 5-methoxy gramine (6.24 g) and commercially available methyl 2-nitro-propionate (4.07 g) in a mixture of toluene (50 ml) and N,N-dimethylformamide (2 ml) is refluxed for one day while bubbling argon through the reaction mixture. The solvent is evaporated, the residue is taken up in dichloromethane (300 ml), is washed subsequently with 2 M aqueous HCl, 2 M aqueous NaOH, and water, is dried and concentrated. Column chromatography of the residue (toluene-acetone, 98:2→95:5) gives the title compound (3.42 g, 38%). M.p. 109-110° C. (from ethyl acetate-light petroleum).

Aufarbeitung

  1. temperatureis refluxed for one day
  2. customwhile bubbling argon through the reaction mixture
  3. customThe solvent is evaporated
  4. washis washed subsequently with 2 M aqueous HCl, 2 M aqueous NaOH, and water
  5. customis dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ffebdf8f25ec48f09844c8657f58608f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530493B2

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