Triethylamine → (1R*,2R*,5S*,6R*)-8-Benzyl-2-[3,5-bis(trifluoromethyl)benzoyloxy]-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octane

HRID 2088096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088096
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:10]([OH:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:39][C:40]([F:55])([F:54])[C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1)[C:44](Cl)=[O:45].C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:17])=[O:18])[CH2:15][C@@:9]1([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:10]([O:25][C:44](=[O:45])[C:43]1[CH:47]=[C:48]([C:50]([F:51])([F:52])[F:53])[CH:49]=[C:41]([C:40]([F:39])([F:54])[F:55])[CH:42]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 516892Sodium BicarbonateHCID 69890353(1R*,2R*,5S*,6R*)-8-Benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

Produkt 1

HCID 86586643(1R*,2R*,5S*,6R*)-8-Benzyl-2-[3,5-bis(trifluoromethyl)benzoyloxy]-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octaneAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (1R*,2R*,5S*,6R*)-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 4; 0.98 g, 2.25 mmol), triethylamine (0.6 ml), N,N-dimethylaminopyridine (100 mg) and 3,5-bis(trifluoromethyl)benzoyl chloride (0.6 ml, 3.33 mmol) in dry dichloromethane (10 ml) was stirred at room temperature for 6 days. The reaction mixture treated with saturated aqueous NaHCO3 and extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 5-30%) to give the title compound (1.05 g, 69%).

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 5-30%)

Quellen und Nachweise

ORD-Eintrag
ord-5fd95c5c464b49d0a243b45da076a18a
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

Notizen zur Reaktion

Wird geladen…