Methyl iodide → HCID 178496620, Verbindung

HRID 1506249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506249
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[H-].[Na+].[CH2:18]1OCCOCCOCCOCCOC1.IC>O1CCCC1.CO>[CH3:18][O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 178418329HCID 178418329, Verbindung

Produkt 1

HCID 178496620HCID 178496620, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl (trans-4-hydroxycyclohexyl)carbamate (1.0 g, 4.6 mmol) in tetrahydrofuran (20 mL) was stirred with sodium hydride (55 wt % dispersion in mineral oil, 24 mg, 6.4 mmol) and 15-crown-5 ether (965 μL) for 30 minutes under cooling with ice and then with iodomethane (289 μL) at room temperature for 1 hour. Methanol (2 mL) was added to the reaction mixture, and the precipitated solid was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1 (v/v)) to give the title compound (708 mg, yield 67%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. customthe precipitated solid was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=8/1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-6b73546813a8493596edb49f86fb9440
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216999B2

Notizen zur Reaktion

Wird geladen…