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4-Methylmorpholine → tert-Butyl 4-[(2E)-4-methoxy-4-oxobut-2-en-1-yl]piperidine-1-carboxylate

HRID 1007747
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1007747
C(Cl)(=O)C(Cl)=O.[C:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21]O)[CH2:16][CH2:15]1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].CN1CCOCC1.[CH3:30][O:31][C:32]([CH:34]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:33]>C(Cl)Cl.CS(C)=O>[C:7]([N:14]1[CH2:15][CH2:16][CH:17]([CH2:20]/[CH:21]=[CH:34]/[C:32]([O:31][CH3:30])=[O:33])[CH2:18][CH2:19]1)([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 65578Oxalyl chlorideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Produkt 1

HCID 10446560tert-Butyl 4-[(2E)-4-methoxy-4-oxobut-2-en-1-yl]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of oxalyl chloride (11.8 g) in methylene chloride (180 ml) is cooled to −78° C. and dimethyl sulfoxide (DMSO) (8.9 ml) is added dropwise. The solution is stirred at −78° C. for about 3 minutes and a solution of N-BOC-2-(piperidin-4-yl)ethanol (14.3 g) in methylene chloride (250 ml) is added over a period of about 10 minutes. The solution is stirred for about 1 hour and N-methyl morpholine (21.6 g) is added over a period of about 15 minutes. The solution is allowed to warm to room temperature and, after about 30 minutes, methyl (triphenylphosphoranylidene) acetate (68.6 g) is added. The solution is stirred at room temperature for about 18 hours, evaporated in vacuo and the residue taken up in ethyl acetate. The ethyl acetate solution is washed with water, 5% HCl, 5% sodium hypochlorite solution, water, brine, dried over sodium sulfate, filtered and evaporated in vacuo to give methyl 4-(N-BOC-piperidin-4-yl)trans-crotonate.

Aufarbeitung

  1. stirringThe solution is stirred for about 1 hour
  2. temperatureto warm to room temperature and, after about 30 minutes
  3. stirringThe solution is stirred at room temperature for about 18 hours
  4. customevaporated in vacuo
  5. washThe ethyl acetate solution is washed with water, 5% HCl, 5% sodium hypochlorite solution, water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-26ccb9ff8ec941288713bd875701d0ba
Quelldatensatz
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06797700B2

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