Allyl bromide → HCID 11577557, compound

HRID 2114618Notes

Reaction equation

HRID 2114618 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

5

Reactant 2

HCID 7841Allyl bromideHCID 9845477HCID 9845477, compound

Product 1

HCID 11577557HCID 11577557, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6342AcetonitrileSolvent

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.

Workup

  1. customSolvents were evaporated
  2. additionThe residue was treated with ether several times
  3. customto obtain an oil, which
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-c7d47dc3ed464d69926c14c951587456
Source dataset
uspto-grants-2008_10
Patent number
US07435742B2

Reaction notes

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