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Ethyl Acetate → (3R,4S)-4-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-piperidine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

HRID 2428192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2428192
CO[Na].[CH3:4][O:5][C:6]([CH:8]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:9]1)=[O:7].CCOC(C)=O>CO>[CH3:4][O:5][C:6]([C@@H:8]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][C:24]3[C:29]([Cl:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[Cl:32])=[CH:16][CH:15]=2)[CH2:12][CH2:11][N:10]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:9]1)=[O:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 671487224-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl esterHCID 178418582HCID 178418582, Verbindung2×

Produkt 1

HCID 67148356(3R,4S)-4-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-piperidine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl EsterAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

MeONa (2.27 g, 42 mmol) was added to a sol. of compounds D5 (22.6 g, 42 mmol) in MeOH (200 mL). The mixture was stirred at 70° C. for 6 h, and MeONa (2.27 g, 42 mmol) was added again. The mixture was stirred at 70° C. for 2 days, and was allowed to cool to rt. EtOAc was added, and the resulting mixture was washed with aq. 1M HCl and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 5:95→10:90) yielded the title compound (10.7 g, 47%). LC-MS: tR=1.19 min, ES+=538.39.

Aufarbeitung

  1. stirringThe mixture was stirred at 70° C. for 2 days
  2. temperatureto cool to rt
  3. washthe resulting mixture was washed with aq. 1M HCl and brine
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (MeOH/CH2Cl2 5:95→10:90)

Quellen und Nachweise

ORD-Eintrag
ord-bd4d4809daea4306a7e37d0ee08b8df4
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07968720B2

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