Reaktion #68283

Reaktionsgleichung

1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methaneamine

methyl 1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)-4-oxopiperidine-2-carboxylate

sodium hydrogen carbonate

sodium triacetoxyborohydride

→

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

Ausbeute 45.1%

Lösungsmittel

acetic acid

acetic acid

dichloromethane

dichloromethane

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   workup.STIRRINGstirred for 2.5 hours
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed with aqueous saturated sodium chloride solution
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigethe solvent was removed under reduced pressure
8. 8
   SonstigeThe residue thus obtained
9. 9
   Sonstigewas purified by basic silica gel column chromatography [eluent; chloroform:methanol=50:1]

Vorschrift

To 10 mL of a dichloromethane solution containing 0.10 g of methyl 1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)-4-oxopiperidine-2-carboxylate, 2 mL of a dichloromethane solution containing 55 mg of 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methaneamine and 32 μL of acetic acid were added at room temperature, and stirred at the same temperature for 1 hour, thereafter, 8 μL of acetic acid was further added, and stirred for 2.5 hours. To the reaction mixture, 59 mg of sodium triacetoxyborohydride was added, and stirred for 1 hour. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added. The organic layer was separated, 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 basic silica gel column chromatography [eluent; chloroform:methanol=50:1], to give 64 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 as a white foam.

Quelle