1,2,3,4-Tetrahydroquinoline → 8-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonate

HRID 599347Notes

Reaction equation

HRID 599347 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.ClC(Cl)(O[C:15](=[O:21])OC(Cl)(Cl)Cl)Cl.Cl.[F:24][C:25]([S:28]([O:31][C:32]1[CH2:38][CH:37]2[NH:39][CH:34]([CH2:35][CH2:36]2)[CH:33]=1)(=[O:30])=[O:29])([F:27])[F:26].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.ClCCl>[F:27][C:25]([F:24])([F:26])[S:28]([O:31][C:32]1[CH2:33][CH:34]2[N:39]([C:15]([N:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:4][CH2:3][CH2:2]3)=[O:21])[CH:37]([CH2:36][CH2:35]2)[CH:38]=1)(=[O:30])=[O:29]

Participants

7

Reactant 4

HCID 694601,2,3,4-TetrahydroquinolineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 866321808-Azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethylsulfonate hydrochloride

Product 1

HCID 866321828-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonateYield 274.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

1.13 g of 1,2,3,4-tetrahydroquinoline, 85 ml of dichloromethane and 1.54 ml of triethylamine are placed in a 250 ml three-necked flask under a nitrogen atmosphere. 0.834 g of triphosgene is added at 0° C., and the reaction is then left to stir at ambient temperature for 4 h. 2.27 g of 8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethylsulfonate hydrochloride and 1.19 ml of triethylamine are subsequently added and the reaction mixture is then refluxed for 18 h. 200 ml of a saturated aqueous solution of sodium hydrogen carbonate are added and the aqueous phase is extracted three times with dichloromethane. The organic phases are combined, dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed on silica gel with an 8/2 mixture of heptane/ethyl acetate. 3.21 g of 8-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonate are obtained.

Workup

  1. waitthe reaction is then left
  2. temperaturethe reaction mixture is then refluxed for 18 h
  3. extractionthe aqueous phase is extracted three times with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue is chromatographed on silica gel with an 8/2 mixture of heptane/ethyl acetate

Sources & evidence

ORD record
ord-f2f1460a552046678ef6474c0f62f81a
Source dataset
uspto-grants-2011_03
Patent number
US07897773B2

Reaction notes

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