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

반응식

HRID 41057 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ffebdf8f25ec48f09844c8657f58608f
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530493B2

연결된 노트

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