Water → 2-(1-Tert-butoxycarbonylindol-3-yl)propionitrile

HRID 12219

Reaktionsgleichung

Reaktionsgleichung von HRID 12219
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C:18]#[N:19])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][Si]([N-][Si](C)(C)C)(C)C.[Na+].IC.O>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]([C:18]#[N:19])[CH3:20])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 15378323tert-Butyl 3-(cyanomethyl)-1H-indole-1-carboxylate

Produkt 1

HCID 252230692-(1-Tert-butoxycarbonylindol-3-yl)propionitrileAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred solution of 3-cyanomethyl-indole-1-carboxylic acid tert-butyl ester (2.15 g, 8.39 mmol) in THF (40 ml) was cooled to −78° C. under an argon atmosphere. Sodium bis(trimethylsilyl)amide (1 M in THF, 10 ml, 10 mmol) was added thereto and the cold solution was stirred for 30 minutes. Iodomethane (627 uL, 10 mmol) was added thereto and the reaction mixture was stirred 1.5 hr while gradually warming to 0° C. H2O (100 ml) was added thereto and the solution was brought to RT and diluted with EtOAc (250 ml). The aqueous layer was removed and extracted with EtOAc (250 ml). The combined organic layers were washed with aqueous HCl (1N, 3×50 ml), followed by brine, then dried over MgSO4, filtered, and concentrated to an orange oil. Purification via column chromatography (hexanes:ethyl acetate) gave 3-(cyano-methyl-methyl)-indole-1-carboxylic acid tert-butyl ester (1.8 g).

Aufarbeitung

  1. stirringthe reaction mixture was stirred 1.5 hr
  2. customwas brought to RT
  3. customThe aqueous layer was removed
  4. extractionextracted with EtOAc (250 ml)
  5. washThe combined organic layers were washed with aqueous HCl (1N, 3×50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to an orange oil
  9. customPurification via column chromatography (hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1a045f84366a4f88ac017f6c5af9c4fc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727985B2

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