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Sodium Sulfite → (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid

HRID 2186383
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2186383
[Mn]([O-])(=O)(=O)=O.[K+].[O:7]=[C:8]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1)[CH2:9][CH2:10][C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C@@H:12]1[CH2:24][CH:25]=[O:26].S([O-])([O-])=[O:40].[Na+].[Na+]>O.CC(C)=O>[O:7]=[C:8]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1)[CH2:9][CH2:10][C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][C@@H:12]1[CH2:24][C:25]([OH:40])=[O:26]
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Komponenten

6

Edukt 3

HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 86758164(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde

Produkt 1

HCID 70176189(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acidAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180
Acetone
Lösungsmittel
2×
HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 0.85 g of potassium permanganate in 25 cm3 of water and 120 cm3 of acetone was added over approximately 1 hour, with stirring and at a temperature in the region of 25° C., to a solution of 1.2 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde in 60 cm3 of acetone. The mixture was stirred for 3 hours at this same temperature and then cooled to approximately 10° C. A solution of 5 g of sodium sulfite in 200 cm3 of water was added to the reaction mixture and then the mixture obtained was filtered through celite. The acetone of the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then the evaporation residue was taken up in 200 cm3 of water and washed with 200 cm3 of diethyl ether. The aqueous phase was separated by settling, acidified with citric acid in the solid state to a pH in the region of 3-4 and extracted with 200 cm3 of diethyl ether. The ethereal solution, separated by settling, was dried over magnesium sulfate, filtered, and evaporated under the above conditions. 0.74 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid was obtained in the form of a yellow solid.

Aufarbeitung

  1. customthe mixture obtained
  2. filtrationwas filtered through celite
  3. customThe acetone of the filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  4. washwashed with 200 cm3 of diethyl ether
  5. customThe aqueous phase was separated
  6. extractionextracted with 200 cm3 of diethyl ether
  7. customThe ethereal solution, separated
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under the above conditions

Quellen und Nachweise

ORD-Eintrag
ord-bc4c849f1d374474abdd7aa80bec5d83
Quelldatensatz
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06403610B1

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