Reaktion #68117

Reaktionsgleichung

sodium hydrogen carbonate

(7-(difluoromethoxy)-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate

sodium triacetoxyborohydride

→

tert-butyl (1-(2-(7-(difluoromethoxy)-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate

Ausbeute 0.1%

Lösungsmittel

chloroform

Water

acetic acid

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred for 40 min
3. 3
   Sonstigethe organic layer was separated
4. 4
   Waschenwashed sequentially with water and aqueous saturated sodium chloride solution
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was removed under reduced pressure
7. 7
   SonstigeThe residue thus obtained
8. 8
   Sonstigewas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3]

Vorschrift

To 1.5 mL of dichloromethane solution containing 0.12 g of (7-(difluoromethoxy)-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 0.16 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 15 μL of acetic acid were added, and stirred for 5 min. To the reaction mixture, 0.14 g of sodium triacetoxyborohydride was added, and stirred for 40 min. Water, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, washed sequentially with water and 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; hexane:ethyl acetate=2:3], to give 0.19 mg of tert-butyl (1-(2-(7-(difluoromethoxy)-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate as a colorless oil.

Quelle