Methyl 2-(3,5-bis(trifluoromethyl)phenyl)-2-diazoacetate → (1R*,2R*,5R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]-(methoxycarbonyl)methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088165

Reaktionsgleichung

Reaktionsgleichung von HRID 2088165
[N+](=[C:3]([C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5])=[N-].[CH2:22]([N:29]1[C@@H:34]2[CH2:35][CH2:36][C@@:30]1([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:31]([OH:37])[CH2:32][CH2:33]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:22]([N:29]1[C@@H:34]2[CH2:35][CH2:36][C@@:30]1([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:31]([O:37][C@H:3]([C:4]([O:6][CH3:7])=[O:5])[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1)[CH2:32][CH2:33]2)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

5

Edukt 2

HCID 54200568Methyl 2-(3,5-bis(trifluoromethyl)phenyl)-2-diazoacetateHCID 69688994(1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

Produkt 1

HCID 86586700(1R*,2R*,5R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]-(methoxycarbonyl)methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 168478Rhodium acetateKatalysatorHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

Slow addition of methyl 2-diazo-2-(3,5-bis(trifluoromethyl)phenyl)acetate (504 mg, 1.61 mmol) as a solution in benzene (3 ml) to (1R*,2R*,5R*)-8-benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 9; 430 mg, 1.47 mmol) in benzene (3 ml) was carried out in the presence of catalytic rhodium acetate (5 mg) at reflux under N2. The reaction mixture was concentrated in vacuo to give a green oil then purified by flash column chromatography [15% ethyl acetate in iso-hexane] to give the title compound as a yellow oil (mainly 1 isomer)(735 mg, 87%).

Aufarbeitung

  1. temperatureat reflux under N2
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a green oil
  4. customthen purified by flash column chromatography [15% ethyl acetate in iso-hexane]

Quellen und Nachweise

ORD-Eintrag
ord-75968bcb1d1949dcb7cde7fe288eb8f2
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

Verknüpfte Notizen

Wird geladen…