Reaktion #68284

Reaktionsgleichung

sodium hydroxide

methanol

methyl 4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate

sodium hydroxide

hydrochloric acid

→

1-(2-(6-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-7-oxo-2,6-diazabicyclo(3.2.1)oct-2-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one

Ausbeute 16.0%

Lösungsmittel

diethyl ether

ethyl acetate

water

diethyl ether

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   workup.STIRRINGstirred at the sane temperature for 1 hour and 50 min
3. 3
   Temperaturcooling
4. 4
   Sonstigethe solvent was removed under reduced pressure, water, ethyl acetate and diethyl ether
5. 5
   workup.ADDITIONwere added
6. 6
   Filtrationthe resulting solid (A′) was filtered
7. 7
   SonstigeAlso, the solvent of the filtrate (B′) was removed under reduced pressure
8. 8
   SonstigeTo the residue thus obtained
9. 9
   Sonstigethe organic layer was separated
10. 10
    Sonstigethe solvent was removed under reduced pressure
11. 11
    SonstigeTo the residue thus obtained
12. 12
    Filtrationthe resulting solid (B) was filtered

Vorschrift

To 5 mL of a methanol solution containing 60 mg of methyl 4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidine-2-carboxylate, 0.2 mL of 20% aqueous sodium hydroxide solution was added at room temperature, and stirred for 1 hour and 10 min. Further, 0.5 mL of 20% aqueous sodium hydroxide solution was added at room temperature, and stirred at the sane temperature for 1 hour and 50 min. The reaction mixture was adjusted to pH 6.2 with 2 mol/L hydrochloric acid under water-cooling, the solvent was removed under reduced pressure, water, ethyl acetate and diethyl ether were added, and the resulting solid (A′) was filtered. Also, the solvent of the filtrate (B′) was removed under reduced pressure. To the residue thus obtained, water, ethyl acetate and diethyl ether were added, the organic layer was separated, and the solvent was removed under reduced pressure. To the residue thus obtained, hexane and diethyl ether were added, and the resulting solid (B) was filtered to give 9 mg of 1-(2-(6-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)-7-oxo-2,6-diazabicyclo(3.2.1)oct-2-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a pale yellow solid.

Quelle