1,10-Phenanthroline → (R)-3-(5,5-Dioxo-5H-5lambda6-dibenzothiophen-3-yloxy)-1-aza-bicyclo[2.2.2]octane

HRID 553049Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12](Br)=[CH:13][C:8]=3[S:7](=[O:16])(=[O:15])[C:6]=2[CH:17]=1.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C@@H:20]([OH:26])[CH2:19]2.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[O:15]=[S:7]1(=[O:16])[C:6]2[CH:17]=[CH:2][CH:3]=[CH:4][C:5]=2[C:9]2[CH:10]=[CH:11][C:12]([O:26][C@@H:20]3[CH:21]4[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]4)[CH2:19]3)=[CH:13][C:8]1=2

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 3,7-dibromodibenzothiophene-5,5-dioxide (0.60 g, 1.75 mmol; see J. Med. Chem. 1978, 21, 1084), (R)-(−)-quinuclidin-3-ol (280 mg, 2.2 mmol; Acros), copper (I) iodide (33 mg, 0.17 mmol; Aldrich), 1,10-phenanthroline (63 mg, 0.35 mol; Aldrich) and powdered cesium carbonate (0.86 g, 2.64 mmol; Aldrich) in toluene (2 mL) was heated to 110° C. with vigorous stirring for 30 h. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth, rinsing with ethyl acetate and dichloromethane, and the residue purified by flash chromatography (80 g silica gel, 1:10:89 NH4OH-MeOH—CH2Cl2) to afford the title compound (0.23 g, 0.67 mmol; 38% yield): MS (DCI/NH3): m/z 342 (M+1)+.

Aufarbeitung

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered through diatomaceous earth
washrinsing with ethyl acetate and dichloromethane
customthe residue purified by flash chromatography (80 g silica gel, 1:10:89 NH4OH-MeOH—CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-23bb82a4d8734297b03143a522c718ca
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07951791B2

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