تفاعل #68156

معادلة التفاعل

sodium hydrogen carbonate

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

(6-chloro-2-oxoquinolin-1(2H)-yl)acetaldehyde

sodium triacetoxyborohydride

→

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

المردود 60.1%

المذيبات

acetic acid

chloroform

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   أخرىthe organic layer was separated
3. 3
   استخلاصthe aqueous layer was extracted with chloroform
4. 4
   غسيلwashed with aqueous saturated sodium chloride solution
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   أخرىthe solvent was removed under reduced pressure
7. 7
   أخرىThe residue thus obtained
8. 8
   أخرىwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; ethyl acetate]

الإجراء التجريبي

To 4 mL of a chloroform solution containing 0.68 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate, 0.44 g of (6-chloro-2-oxoquinolin-1(2H)-yl)acetaldehyde and 40 μL of acetic acid were added, then, to the reaction mixture, 0.62 g of sodium triacetoxyborohydride was added and stirred at room temperature for 2 nights. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, 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 silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; ethyl acetate], to give 0.65 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(6-chloro-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white foam.

المصدر