Reaktion #68001

Reaktionsgleichung

sodium hydrogen carbonate

tert-butyl piperazine-1-carboxylate

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

sodium triacetoxyborohydride

→

tert-butyl 4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-1-carboxylate

Lösungsmittel

acetic acid

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 1 hour
2. 2
   Sonstigethe organic layer was separated
3. 3
   WaschenThe organic layer was washed with an aqueous saturated sodium chloride solution
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 [silica gel; Silica gel 60N manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate]

Vorschrift

Into 5 mL of chloroform, (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde was dissolved, thereto were added 135 mg of tert-butyl piperazine-1-carboxylate and 43.6 mg of acetic acid, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with 231 mg of sodium triacetoxyborohydride, and stirred for 1 hour. Thereto was added an aqueous saturated sodium hydrogen carbonate solution, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60N manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate] to obtain 173 mg of a yellow oily substance, tert-butyl 4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-1-carboxylate.

Quelle