Water → Methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate

HRID 1182360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182360
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=O)[C:5]([N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:6][CH:7]=1.C[O-].[Na+].O>C(=O)(OC)OC.CO>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:9][CH2:10][CH2:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:21][C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86604826HCID 86604826, Verbindung

Produkt 1

HCID 69425256Methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylateAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 12021Dimethyl CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of methyl 5-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]pentanoate (840 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (874 mg), and the mixture was heated at 65° C. for 3 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added, and then the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the residue, and then the obtained residue was washed with hexane-ethyl acetate to give methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (741 mg) as yellow crystals.

Aufarbeitung

  1. customwas returned to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
  7. customto obtain the residue
  8. washthe obtained residue was washed with hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c4d8b66a5a0f41c9a471bd169a5231ed
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288654B2

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