1-((2-Bromoethoxy)methyl)-4-methoxybenzene → HCID 67311654, Verbindung
Reaktionsgleichung
Br[CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([O:22][C:23]([C:25]1([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:15]2>CC#N>[CH:23]([O-:24])=[O:22].[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:4][CH2:3][CH2:2][N+:14]23[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]2)[C@@H:16]([O:22][C:23]([C:25]2([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])[CH2:15]3)=[CH:7][CH:8]=1Komponenten
4
Versuchsvorschrift
A mixture of 1-(2-bromo-ethoxymethyl)-4-methoxy-benzene (42 mg) and 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (50 mg) in MeCN (1 mL) was stirred at room temperature for 16 h then heated to 80° C. under nitrogen overnight. A further 1.1 equivalents of 1-(2-bromo-ethoxymethyl)-4-methoxy -benzene were added and the mixture was heated at 80° C. for a further 48 h. The volatiles were evaporated and the crude product was purified by silica gel chromatography eluting with 0-10% of a 10% conc. NH3/MeOH solution in dichloromethane give 61 mg of an oil that was purified further by reverse phase HPLC (Gemini 5 μM C6 phenyl column) eluting with 5-95% MeOH/H2O containing 0.1% formic acid over 30 min with UV detection at 220 nm. The relevant fractions were combined and evaporated to afford the title compound (34 mg) as an oil.