Methanol → 1-Adamantyl carbamate

HRID 2092023

Reaktionsgleichung

Reaktionsgleichung von HRID 2092023
[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.ClC(Cl)(Cl)[C:14]([N:16]=C=O)=[O:15].CO.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:14](=[O:15])([O:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)[NH2:16]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 641521-AdamantanolHCID 76400Trichloroacetyl isocyanate

Produkt 1

HCID 124376461-Adamantyl carbamateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Adamantanol (1.52 g, 10.0 mmol) in dichloromethane (30 mL) was mixed with trichloroacetyl isocyanate (1.40 mL, 11.8 mmol) at 0° C., then warmed to room temperature and stirred for 2 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure, and the resulting crude reaction product was mixed with methanol (15 mL) and saturated aqueous potassium carbonate and stirred at 50° C. for 1 day. After completion of the reaction, the methanol was removed by vacuum distillation, and the residue was filtered. The resulting solid was washed with water and dried under reduced pressure to give the desired product (74% yield, 2 steps).

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe reaction solution was evaporated under reduced pressure
  3. customthe resulting crude reaction product
  4. stirringstirred at 50° C. for 1 day
  5. customAfter completion of the reaction
  6. customthe methanol was removed by vacuum distillation
  7. filtrationthe residue was filtered
  8. washThe resulting solid was washed with water
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4d49707e34924196974f4073021abddf
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440666B2

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