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Dimethyl Sulfoxide → (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde

HRID 2186384
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2186384
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][C@@H:14]1[C@H:19]([CH2:20][CH2:21][CH:22]([OH:35])[C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17][N:16]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:15]1.C(N(CC)CC)C>ClCCl>[O:35]=[C:22]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:21][CH2:20][C@@H:19]1[CH2:18][CH2:17][N:16]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:15][C@@H:14]1[CH2:13][CH:12]=[O:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69353248(3R,4R)-3-(2-hydroxyethyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine

Produkt 1

HCID 86758164(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde
Ausbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

A mixture of 13.7 g of dimethyl sulfoxide in 65 cm3 of dichloromethane was slowly added, with stirring and under an inert atmosphere, to a solution, cooled to a temperature in the region of −60° C., of 8.3 cm3 of oxalyl chloride in 65 cm3 of dichloromethane. After stirring the mixture for 15 minutes, 10 g of (3R,4R)-3-(2-hydroxyethyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine, dissolved in 65 cm3 of dichloromethane, were slowly added. After stirring the mixture for 30 minutes, 61.7 cm3 of triethylamine, dissolved in 65 cm3 of dichloromethane, were finally added dropwise. The mixture was stirred for a further 3 hours at approximately −60° C. and then poured onto 400 cm3 of ice-cold water. After separating the mixture by settling, the organic phase was washed with 400 cm3 of a 10% (by mass) aqueous citric acid solution and then dried over magnesium sulfate, filtered, and evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 9.95 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetaldehyde were obtained in the form of an. oil with a brown color.

Aufarbeitung

  1. additionwas slowly added
  2. stirringAfter stirring the mixture for 15 minutes
  3. additionwere slowly added
  4. stirringAfter stirring the mixture for 30 minutes
  5. additionwere finally added dropwise
  6. stirringThe mixture was stirred for a further 3 hours at approximately −60° C.
  7. customAfter separating the mixture
  8. washthe organic phase was washed with 400 cm3 of a 10% (by mass) aqueous citric acid solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-ee99234dfd8844c2b160c69c4cf0bf66
Quelldatensatz
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06403610B1

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