Methanol → Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate

HRID 1390832

反応式

HRID 1390832 の反応式
[CH2:1]([O:3][C:4]([C:6]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)[CH:8](O)[N:7]1[CH:21]=[O:22])=[O:5])[CH3:2].CO.[H][H]>[Ni].C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:5])[C:6]([NH:7][CH:21]=[O:22])([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][C:9]1[C:11]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:17][CH:8]=1)[CH3:2]

参加物

6

反応物 3

HCID 887MethanolHCID 128784961-Formyl-5-hydroxy-4-[2-nitrophenyl]-pyrrolidine-2,2-dicarboxylic acid diethylesterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 292164Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate収率 97.9%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 176Acetic Acid溶媒

実験手順

50.0 g (0.13 mol) of the compound of Example 4 in 500 ml. of methanol and 1 ml of acetic acid was hydrogenated in a rocking autoclave at room temperature and 200 psi in the presence of 6 g. of Raney nickel. After the hydrogen uptake (3 equivalents) was complete the filtered reaction mixture was concentrated in vacuo to a volume of 140 ml. Toluene (600 ml.) was added and the remaining methanol was removed by azeotropic distillation. The mixture was heated at reflux for an additional 30 minutes and then allowed to cool to room temperature. The precipitate was collected, washed with toluene and dried to yield 42.3 g (97%) of white crystals, m.p. 179-180° (lit. m.p. 179°). The analytical sample was prepared by recrystallization from ethaniol: m.p. 180-181°.

後処理

  1. customwas hydrogenated in a rocking autoclave at room temperature
  2. customthe filtered reaction mixture
  3. concentrationwas concentrated in vacuo to a volume of 140 ml
  4. additionToluene (600 ml.) was added
  5. customthe remaining methanol was removed by azeotropic distillation
  6. temperatureThe mixture was heated
  7. temperatureat reflux for an additional 30 minutes
  8. customThe precipitate was collected
  9. washwashed with toluene
  10. customdried

出典と根拠

ORDレコード
ord-b74a3c1de5cf4d8186054f1480f7ec75
出典データセット
uspto-grants-1979_02
特許番号
US04140697

関連ノート

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