Methyl iodide → HCID 178501214, Verbindung

HRID 1019907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1019907
[CH3:1]C([O-])(C)C.[K+].[CH3:7][O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][C:19]2[CH:28]=[CH:27][C:22]3[O:23][CH2:24][CH2:25][O:26][C:21]=3[CH:20]=2)[CH2:13][CH2:12]1)=[O:10].CI>CN(C)C=O>[CH3:7][O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([N:17]([CH2:18][C:19]2[CH:28]=[CH:27][C:22]3[O:23][CH2:24][CH2:25][O:26][C:21]=3[CH:20]=2)[CH3:1])[CH2:13][CH2:12]1)=[O:10]

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 23665647Potassium tert-butoxideHCID 178501211HCID 178501211, Verbindung

Produkt 1

HCID 178501214HCID 178501214, VerbindungAusbeute 1.616 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium tert-butylate (35 mg, 0.31 mmol, 1.0 eq) is added at room temperature to a stirred solution of trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amino]-cyclohexanecarboxylic acid methyl ester (100 mg, 0.31 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by methyl iodide (10 μL, 0.16 mmol, 0.5 eq). After 15 hours stirring at room temperature methyl iodide (10 μL, 0.16 mmol, 0.5 eq) is added again. After 4 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×5 mL) and water (5 mL). The combined organic layers are washed with brine (5 mL), dried over sodium sulfate, filtered and concentrated to afford trans-4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-methyl-amino]-cyclohexanecarboxylic acid methyl ester as a brown oil (1.60 g, 98% yield).

Aufarbeitung

  1. additionis added again
  2. customsolvent is evaporated
  3. extractionthe residue is extracted with ethyl acetate (3×5 mL) and water (5 mL)
  4. washThe combined organic layers are washed with brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b7b75e53d5a3445eb1d3724d5e73d5a3
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716280B2

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