Ammonium Chloride → HCID 178461575, Verbindung

HRID 1913549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913549
[CH3:1][C@H:2]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[C:5](=[O:18])[CH2:4][CH2:3]1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([N:36]2[CH:40]=[C:39]([CH:41]=O)[N:38]=[CH:37]2)[CH2:32][CH2:31]1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C@H:2]1[CH2:7][NH:6][C:5](=[O:18])/[C:4](=[CH:41]/[C:39]2[N:38]=[CH:37][N:36]([C@H:33]3[CH2:34][CH2:35][C@H:30]([CH3:29])[CH2:31][CH2:32]3)[CH:40]=2)/[CH2:3]1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 22872605Benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylateHCID 178461291HCID 178461291, Verbindung

Produkt 1

HCID 178461575HCID 178461575, VerbindungAusbeute 55,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate (Org. Lett, 2009, Vol. 11, p. 5410) (772 mg) was dissolved in tetrahydrofuran (15 mL). To the solution, lithium hexamethyldisilazide (LHMDS, 1 N tetrahydrofuran solution, 3.12 mL) was added dropwise at −78° C., and the mixture was stirred for 1 hour. Subsequently, a solution of 1-(trans-4-methylcyclohexyl)-1H-imidazole-4-carbaldehyde (600 mg) in tetrahydrofuran (5 mL) was added dropwise thereto at −78° C., and the mixture was stirred at 0° C. for 3 hours. To the reaction solution, aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate-ethyl acetate/methanol=92/8) to obtain the title compound (500 mg).

Aufarbeitung

  1. stirringat −78° C., and the mixture was stirred at 0° C. for 3 hours
  2. extractionorganic matter was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a crude product
  7. customThis crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate-ethyl acetate/methanol=92/8)

Quellen und Nachweise

ORD-Eintrag
ord-a4395665ce1a44eeb3e765375bcf5391
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609710B2

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