Citric Acid → 4-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

HRID 228037

Reaktionsgleichung

Reaktionsgleichung von HRID 228037
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([OH:19])=O)([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)C#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:45][C:46]1[CH:53]=[CH:52][C:49]([NH:50][CH3:51])=[CH:48][CH:47]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([N:50]([C:49]3[CH:52]=[CH:53][C:46]([Cl:45])=[CH:47][CH:48]=3)[CH3:51])=[O:19])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

8

Edukt 5

HCID 311Citric AcidHCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 702724-Chloro-N-methylbenzenamineHCID 231507384-{[(Tert-butoxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylic acid

Produkt 1

HCID 231505174-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-tert-Butoxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (101 mg) was dissolved in dichloromethane (2 mL). To this solution, trichloroacetonitrile (74.0 μL) and triphenylphosphine (196 mg) in dichloromethane (1.5 mL) were sequentially added and the mixture was stirred at room temperature for 2 hours. This was followed by addition of triethylamine (0.18 mL) and 4-chloro-N-methylaniline (98.6 μL) and stirring at room temperature for additional 5.5 hours. The reaction mixture was then poured into aqueous citric acid (5 mL) and was extracted with ethyl acetate (3×10 mL). The ethyl acetate extracts were combined, washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=2:1) to give 4-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (91.4 mg) as a white powder.

Aufarbeitung

  1. stirringstirring at room temperature for additional 5.5 hours
  2. extractionwas extracted with ethyl acetate (3×10 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by a silica gel column (eluant:hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-3233b079ee80401286c5780430e054a0
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560569B2

Verknüpfte Notizen

Wird geladen…