Methylamine → 3-Methyl-7-p-toluenesulfonyl-3,7-diazabicyclo[3.3.0]oct-1(5)-ene

HRID 1534653Notes

Reaction equation

HRID 1534653 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.[CH3:20][NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][N:21]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

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 199082361-p-Toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrroline

Product 1

HCID 199100673-Methyl-7-p-toluenesulfonyl-3,7-diazabicyclo[3.3.0]oct-1(5)-eneYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-p-toluenesulfonyl-3,4-bis(bromomethyl)-3-pyrroline (6.1 g) was dissolved in acetonitrile (70 ml), 40% methylamine aqueous solution (1.5 ml) and anhydrous potassium carbonate powder (16 g) were added and stirred for 2 hours at room temperature. The solid was filtered off and the filtrate was purified by silicagel column chromatography to yield 3-methyl-7-p-toluenesulfonyl-3,7-diazabicyclo[3.3.0]oct-1(5)-ene (0.82 g, yield 20%). 0.8 g of this compound and 0.8 g of phenol were refluxed in 48% hydrobromic acid (15 ml) for 5 hours. The reaction mixture was washed with chloroform (20 ml×3), decolorized with active charcoal. The solvent was distilled off and washed with ethanol-ethylether (1:1) to give the title compound (0.5 g, yield 60%).

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate was purified by silicagel column chromatography

Sources & evidence

ORD record
ord-facdc43951284a2eb2c218c755ae100a
Source dataset
uspto-grants-1992_02
Patent number
US05089621

Reaction notes

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