Hydrochloric Acid → HCID 178455365, Verbindung

HRID 1243182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243182
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:23](Cl)(Cl)=[O:24].Cl>ClCCl>[C:1]([Si:5]([O:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]=[C:23]=[O:24])[CH2:11][CH2:12]1)([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 8471TriethylamineHCID 178455364HCID 178455364, Verbindung

Produkt 1

HCID 178455365HCID 178455365, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine (1.0 g, 4.36 mmol) (from Example 3a supra) and triethylamine (3.04 mL, 21.8 mmol) (Burdick & Jackson) in dichloromethane (30 mL) at 0° C. was added phosgene (˜20% in toluene, 6.4 mL, 13.1 mmol) (Fluka) in one portion. The reaction mixture was stirred at 0° C. for 40 minutes, followed by addition of 0.5N aqueous hydrochloric acid (50 mL). The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexanes (1:9) to give tert-butyl-(trans-4-isocyanato-cyclohexyloxy)-dimethyl-silane. (Yield 0.90 g, 81%).

Aufarbeitung

  1. washThe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate-hexanes (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-cd059f953a6049ca9d167ec48de11218
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115740B2

Notizen zur Reaktion

Wird geladen…