Indole → HCID 69267751, Verbindung

HRID 751524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751524
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([O:14][C:15]([N:17]1[CH:22](C)[CH2:21][C:20](=O)[CH2:19][CH:18]1C)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:27].[Na+].[OH-].[Na+]>C(O)(=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:21]([CH2:26][CH3:27])[CH2:22]1)=[O:16])([CH3:11])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 798IndoleHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 59662193tert-Butyl 2,6-dimethyl-4-oxopiperidine-1-carboxylate

Produkt 1

HCID 69267751HCID 69267751, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Dissolve 1H-Indole (10 g, 50.2 mmol) and 2,6-Dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (8.62 g, 55.2 mmol) in glacial acetic acid (100 mL), add sodium triacetoxyborohydride (15.96 g, 75.3 mmol) and heat the mixture to 70° C. for 20 h. Cool the reaction mixture in an ice bath and made basic with 5N sodium hydroxide solution. Extract the mixture with methylene chloride, wash with water, brine and dry over sodium sulphate to yield the title compound. Flash chromatography using a gradient of ethyl acetate in hexanes yields the pure product. ESMS m/z (relative intensity) ES(M++H): 329.1.

Aufarbeitung

  1. temperatureCool the reaction mixture in an ice bath
  2. extractionExtract the mixture with methylene chloride
  3. washwash with water, brine
  4. dry with materialdry over sodium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-c784b4ff04ff4b939a6d0528e9b0acf9
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405305B2

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