Sodium borohydride → HCID 58554152, Verbindung

HRID 1630986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1630986
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[C:6]([CH2:7][OH:8])[CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 23091110HCID 23091110, Verbindung

Produkt 1

HCID 58554152HCID 58554152, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-2-(2-methylpyrrolidin-1-yl)benzaldehyde (17 g, 63.4 mmol) in methanol (150 mL) under nitrogen was added sodium borohydride (2.41 g, 63.4 mmol) at 0° C. in portions. The reaction mixture was stirred at RT for 1 hour, then evaporated to remove methanol. The resulting crude was taken up with water (250 mL) and extracted with EtOAc (150 mL). The organic layer was washed with water, then dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (16 g, 93%). 1H NMR (DMSO-d6, 400 MHz) δ 7.53 (1H, d), 7.27 (1H, d), 6.87 (1H, d), 5.22 (1H, t), 4.42 (2H, m), 3.56 (1H, m), 3.36 (1H, m), 2.70 (1H, m), 2.49 (1H, m) 2.09 (1H, m), 1.83 (1H, m), 1.73 (1H, m), 1.47 (1H, m), 0.90 (3H, d).

Aufarbeitung

  1. customevaporated
  2. customto remove methanol
  3. extractionextracted with EtOAc (150 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-059d97b075c448bbbf1321070a48a810
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791142B2

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