Allyl bromide → HCID 11577557, compound

Reaction equation

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:31])[N:11]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH2:12][C:13]1[O:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[CH2:2]2.[CH2:32]([Br:35])[CH:33]=[CH2:34]>C(Cl)(Cl)Cl.C(#N)C>[Br-:35].[CH2:34]([N+:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10](=[O:31])[N:11]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[CH2:12][C:13]1[O:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[CH2:2]2)[CH:33]=[CH2:32]

Participants

Procedure

0.300 g (0.7 mmol) of [2-(3,4-Dimethoxyphenyl)ethyl]-(5-methylfuran-2-ylmethyl)carbamic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester were dissolved in 5 ml of CHCl3 and 3.5 ml of acetonitrile. To this solution 0.30 ml (0.423 g, 3.5 mmol) of allyl bromide were added and the mixture was stirred during 21 hours at room temperature under N2 atmosphere. Solvents were evaporated. The residue was treated with ether several times to obtain an oil, which was redissolved in CHCl3 and evaporated to dryness to give 0.365 g (94.8%) of the title product.