Potassium Sodium Tartrate → N-methoxy-N,2-dimethyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide

HRID 1881939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881939
Cl.[CH3:2][O:3][NH:4][CH3:5].C[Al](C)C.[CH3:10][C:11]([C:24]1[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][N:25]=1)([CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:12]([O:14]CC)=O.C(=O)([O-])O.[Na+].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH3:2][O:3][N:4]([CH3:5])[C:12](=[O:14])[C:11]([CH3:10])([C:24]1[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][N:25]=1)[CH2:17][CH:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

Komponenten

7

Edukt 5

HCID 9357Potassium Sodium TartrateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 16682925TrimethylaluminumHCID 59331482ethyl 2-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate

Produkt 1

HCID 59331471N-methoxy-N,2-dimethyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of N-methoxymethanamine hydrochloride (1.00 g) in toluene (10 mL) was cooled to 0° C., and trimethylaluminum (1.4M hexane solution, 7.36 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 1.5 hr, and a solution (10 mL) of ethyl 2-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate (1.11 g) in toluene was added dropwise thereto. The reaction mixture was stirred at room temperature for 24 hr, saturated aqueous sodium hydrogen carbonate and saturated aqueous Rochelle salt solution were added and the mixture was stirred for 1 hr. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (401 mg, yield 35%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 24 hr
  2. stirringthe mixture was stirred for 1 hr
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-72111d3b809b4ea6a339683779386743
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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