Reaktion #68278

Reaktionsgleichung

sodium triacetoxyborohydride

sodium triacetoxyborohydride

sodium triacetoxyborohydride

1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one

tert-butyl (5-formyl-2-methylphenyl)carbamate

sodium hydrogen carbonate

→

tert-butyl (5-(((1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2-methylphenyl)carbamate

Ausbeute 81.2%

Lösungsmittel

acetic acid

acetic acid

methylene chloride

acetic acid

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred for 10 hours
3. 3
   workup.WAITto stand overnight
4. 4
   workup.STIRRINGstirred for 40 min
5. 5
   workup.STIRRINGstirred at room temperature for 2 hours and 40 min
6. 6
   workup.STIRRINGstirred for 40 min
7. 7
   workup.STIRRINGstirred at room temperature for 2 hours
8. 8
   Sonstigethe organic layer was separated
9. 9
   Extraktionthe aqueous layer was extracted with chloroform
10. 10
    Trocknendried over anhydrous magnesium sulfate
11. 11
    Sonstigethe solvent was removed under reduced pressure
12. 12
    SonstigeThe residue thus obtained
13. 13
    Sonstigewas purified by silica gel column chromatography [eluent; chloroform:methanol=5:1]

Vorschrift

To 10 mL of a methylene chloride solution containing 0.20 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one, 0.19 g of tert-butyl (5-formyl-2-methylphenyl)carbamate and 45 μL of acetic acid were added, and stirred for 30 min. To the reaction mixture, 0.21 g of sodium triacetoxyborohydride was added, and stirred for 10 hours. After allowed to stand overnight, 45 μl of acetic acid was added and stirred for 40 min, then 0.17 g of sodium triacetoxyborohydride was added, and stirred at room temperature for 2 hours and 40 min. 90 μL of acetic acid was further added and stirred for 40 min, then 0.34 g of sodium triacetoxyborohydride was added, and stirred at room temperature for 2 hours. To the reaction mixture, 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, 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=5:1], to give 0.28 g of tert-butyl (5-(((1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)amino)methyl)-2-methylphenyl)carbamate as a pale yellow oil.

Quelle