Reacción #68047

Ecuación de reacción

methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

trifluoroacetic acid

→

methyl 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

Rendimiento 57.5%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and chloroform
3. 3
   workup.ADDITIONwere added
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with chloroform
6. 6
   Lavadowashed with aqueous saturated sodium chloride solution
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure
9. 9
   OtroThe residue thus obtained
10. 10
    Otrowas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Procedimiento

To 2 mL of a chloroform solution containing 0.25 g of methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate, 2 mL of trifluoroacetic acid was added and stirred for 16 hours. The solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and chloroform were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to give 0.12 g of methyl 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate as a white solid.

Fuente