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

HRID 1390832

Reaction equation

HRID 1390832 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-b74a3c1de5cf4d8186054f1480f7ec75
Source dataset
uspto-grants-1979_02
Patent number
US04140697

Linked notes

Loading…