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

反応式

HRID 41057 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 58212093(+/-)-3-(5-methoxy-1H-indol-3-yl)-2-methyl-2-nitro-propionic acid methyl ester収率 38.3%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ffebdf8f25ec48f09844c8657f58608f
出典データセット
uspto-grants-2013_09
特許番号
US08530493B2

関連ノート

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