5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran → HCID 44516993, Verbindung
Reaktionsgleichung
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.Br[CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=1>C(#N)C>[CH:10]([O-:11])=[O:9].[O:35]1[C:31]2[CH:30]=[CH:29][C:28]([CH2:27][CH2:26][N+:1]34[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]3)[C@@H:3]([O:9][C:10]([C:12]3([C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])[CH2:2]4)=[CH:36][C:32]=2[CH2:33][CH2:34]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (126 mg) and 5-(2-bromo-ethyl)-2,3-dihydro-benzofuran (105 mg, 0.46 mmol) in acetonitrile (1.5 mL) was stirred at room temperature for 22 h. The volatiles were evaporated and the residue purified by silica gel chromatography eluting with dichloromethane then 5% then 10% MeOH/dichloromethane. The relevant fractions were combined and evaporated and the residue triturated with dichloromethane to give an off -white foam. Further purification was achieved by reverse-phase HPLC (5-98% MeCN containing 0.1% formic acid) to give the title compound (70 mg) as a white gummy solid.