Water → 1,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepine

HRID 983057

Reaktionsgleichung

Reaktionsgleichung von HRID 983057
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[N:10]O)[C:4]=2[CH:3]=[CH:2]1.CC(C[AlH]CC(C)C)C.[F-].[Na+].O>C(Cl)Cl>[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][NH:10][C:4]=2[CH:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5235Sodium FluorideHCID 14487Diisobutylaluminum hydrideHCID 9156771,5,6,7-Tetrahydro-indol-4-one oxime

Produkt 1

HCID 225617901,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepineAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1,5,6,7-tetrahydro-indol-4-one oxime (1.2 g, 7.7 mmol) in DCM (anhydrous, 250 mL) was added DIBAL-H (1M solution in DCM, 35 mL) at 0° C. under nitrogen. After 2 hours, NaF (7 g) was added followed by water (2.24 g). After 20 mins, the reaction was filtered through celite and the solvent was removed to give 350 mg of 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine as a brown oil.

Aufarbeitung

  1. waitAfter 20 mins
  2. filtrationthe reaction was filtered through celite
  3. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-9a2c8b4b72344aa88edb49d8d0bfed8a
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861418B2

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