Tetrahydrofuran → HCID 69269361, Verbindung

HRID 751526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751526
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH:10]([CH2:23]C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1C[O:34]CC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH:10]([CH2:23][OH:34])[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 69267751HCID 69267751, Verbindung

Produkt 1

HCID 69269361HCID 69269361, VerbindungAusbeute 45,2 %

Versuchsvorschrift

Dissolve 1-(1-tert-Butoxycarbonyl-3-ethyl-piperidin-4-yl)-1H-indole (2.86 g, 7.7 mmol) in TIP (25 ml) and stir at ambient temperature. Add a 1M solution of lithium aluminum hydride in THF (8.5 ml, 8.5 mmol) dropwise via syringe. Stir for two hours, then quench with 0.34 ml water, 0.26 ml 5N sodium hydroxide, and 1.2 ml water. Filter through a pad of Celite®, concentrate to an oil. Purify by flash chromatography to yield the title compound (1.15 g, 45%). ES (M++1): 275.1

Aufarbeitung

  1. stirringStir for two hours
  2. customquench with 0.34 ml water, 0.26 ml 5N sodium hydroxide, and 1.2 ml water
  3. filtrationFilter through a pad of Celite®
  4. concentrationconcentrate to an oil
  5. customPurify by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ece4803ffbf40fea51bcdf117743781
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405305B2

Notizen zur Reaktion

Wird geladen…