Lithium borohydride → HCID 68765623, Verbindung

HRID 1398786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398786
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15][CH2:16][C:17](OCC)=[O:18])[C:12]3[C:22]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:23][CH:24]=[C:25]([Cl:26])[C:11]=3[N:10]=2)=[C:4]([CH3:32])[CH:3]=1.[BH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[C:12]3[C:22]([CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:23][CH:24]=[C:25]([Cl:26])[C:11]=3[N:10]=2)=[C:4]([CH3:32])[CH:3]=1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 68763229Ethyl 4-[2-[(4-bromo-2-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate

Produkt 1

HCID 68765623HCID 68765623, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-[2-[(4-bromo-2-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (2.07 g, 3.97 mmol) in tetrahydrofuran (40 mL) was added lithium tetrahydroborate (260 mg, 11.9 mmol) at 0° C. The mixture was stirred at room temperature for 19 hr, and the reaction was quenched by methanol. The mixture was concentrated in vacuo, neutralized with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from ethyl acetate to give the title compound as a colorless crystal (1.10 g, 2.30 mmol, 58%).

Aufarbeitung

  1. customthe reaction was quenched by methanol
  2. concentrationThe mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-90ce7276d91e4310b6600f367dafbd6a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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