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

HRID 1182363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182363
[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=O)[C:5]([N:8]([CH2:17][CH2:18][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][CH2:18][CH3:19])[CH2:9][CH2:10][CH2:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:20][C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86604827Methyl 5-[(5-bromo-3-formylpyridin-2-yl)(propyl)amino]pentanoate

Produkt 1

HCID 69425413Methyl 3-bromo-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylateAusbeute 99,9 %

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)(propyl)amino]pentanoate (880 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (951 mg), and the mixture was heated at 65° C. for 6 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added thereto, and then the 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 give methyl 3-bromo-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (835 mg) as a yellow oily material.

Aufarbeitung

  1. customwas returned to room temperature
  2. extractionthe 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)

Quellen und Nachweise

ORD-Eintrag
ord-d820e4ccb5034f74b1dafa8e41825f1b
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288654B2

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