Reaktion #68102

Reaktionsgleichung

sodium hydrogen carbonate

(7-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde

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

sodium triacetoxyborohydride

→

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

Ausbeute 92.3%

Lösungsmittel

chloroform

Water

acetic acid

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred for 50 min
3. 3
   SonstigeThe organic layer was separated
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was removed under reduced pressure
6. 6
   SonstigeThe residue thus obtained
7. 7
   Sonstigewas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:3]

Vorschrift

To 2.5 mL of dichloromethane solution containing 83 mg of (7-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde, 0.13 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 25 μL of acetic acid were added, and stirred for 1 hour. To the reaction mixture, 0.12 g of sodium triacetoxyborohydride was added, and stirred for 50 min. Water and chloroform were added, and adjusted to pH 10.0 with aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, 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=1:3], to give 0.19 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)carbamate as a colorless oil.

Quelle