Imidazole → HCID 69270936, Verbindung

HRID 751527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751527
[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:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]>ClCCl>[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][O:24][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69269361HCID 69269361, Verbindung

Produkt 1

HCID 69270936HCID 69270936, VerbindungAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dissolve 3-Hydroxymethyl-4-indol-1-ylpiperidine-1-carboxylic acid tert-butyl ester (1.1 g, 3.3 mmol) in dichloromethane (20 ml). Add imidazole (340 mg, 5.0 mmol) and tert-butyldimethylsilyl chloride (754 mg, 5.0 mmol) and stir at ambient temperature for 72 hours. Dilute with dichloromethane, wash with 1N HCl, water, brine. Dry with sodium sulfate, filter, and concentrate to an oil. Purify by flash chromatography (10% ethyl acetate:hexanes) to yield the title compound (1.48 g, 100%). ES (M++1): 389.2

Aufarbeitung

  1. washwash with 1N HCl, water, brine
  2. dry with materialDry with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate to an oil
  5. customPurify by flash chromatography (10% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-862879a0d4f44f489797437c6c7c5f99
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405305B2

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