Acetonitrile → 3-Ethyl-7-p-toluene sulfonyl-3,7-diazabicyclo [3.3.0]oct-1(5)-ene

HRID 1534651Notes

Reaction equation

HRID 1534651 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C:13]([CH2:15]Br)=[C:12]([CH2:17]Br)[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:26](#[N:28])[CH3:27]>C(N)C>[CH2:26]([N:28]1[CH2:15][C:13]2[CH2:14][N:10]([S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:19])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH2:11][C:12]=2[CH2:17]1)[CH3:27]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 199082361-p-Toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrroline

Product 1

HCID 538485303-Ethyl-7-p-toluene sulfonyl-3,7-diazabicyclo [3.3.0]oct-1(5)-eneYield 39%

Reagents, catalysts & solvents 1

HCID 6341EthylamineSolvent

Procedure

To a solution of 1-p-toluene sulfonyl-3,4-bis (bromomethyl)-3-pyrroline (3.41 g) in acetonitrile (43 ml), 0.73 ml of 70% ethylamine and anhydrous potassium carbonate (8 g) were added and stirred at room temperature for one hour. The solid was filtered off and the filtrate was purified by silicagel column chromatography (CHCl3 --MeOH) to give 3-ethyl-7-p-toluene sulfonyl-3,7-diazabicyclo [3.3.0]oct-1(5)-ene (0.95 g, yield 39%). 0.9 g of this compound was hydrolysized in 20 ml of 48% hydrobromic acid with 1 g of phenol. The hydrolysate was washed with chloroform (30 ml×3) and decolorized with active carbon. The solvent was concentrated and washed with ethanol to give the title compound (0.57 g, yield 62%).

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate was purified by silicagel column chromatography (CHCl3 --MeOH)

Sources & evidence

ORD record
ord-48b9aadf23a544719c76f21c835b365d
Source dataset
uspto-grants-1992_02
Patent number
US05089621

Reaction notes

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