Reaction #68058

Reaction equation

dichloromethane

ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate

trifluoroacetic acid

→

ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate

Yield 94.6%

Solvents

hexane

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe solvent was removed under reduced pressure, chloroform and water
3. 3
   workup.ADDITIONwere added
4. 4
   Temperaturecooling
5. 5
   OtherThe organic layer was separated
6. 6
   Extractionthe aqueous layer was extracted with chloroform
7. 7
   Washwashed sequentially with water and aqueous saturated sodium chloride solution
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   Otherthe solvent was removed under reduced pressure
10. 10
    OtherTo the residue thus obtained
11. 11
    Filtrationthe resulting solid was filtered

Procedure

To 3 mL of a dichloromethane solution containing 0.15 g of ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate, 3 mL of trifluoroacetic acid was added and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, chloroform and water were added, and adjusted to pH 10 with 20% aqueous sodium hydroxide solution, under ice-cooling. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, hexane was added and the resulting solid was filtered to give 0.12 g of ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-5-yl)acrylate as a light brown solid.

Source