반응 #67997

반응 방정식

sodium hydrogen carbonate

1,4-benzodioxane-6-carbaldehyde

tert-butyl (piperidin-4-yl)carbamate

sodium triacetoxyborohydride

→

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

수율 64.3%

용매

acetic acid

chloroform

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGstirred overnight
3. 3
   기타the organic layer was separated
4. 4
   세척The organic layer was washed with an aqueous saturated sodium chloride solution
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   기타the solvent was removed under reduced pressure
7. 7
   기타The residue thus obtained
8. 8
   기타was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane=5:1]

실험 절차

To 20 mL of a chloroform solution containing 2.17 g of 1,4-benzodioxane-6-carbaldehyde and 2.67 g of tert-butyl (piperidin-4-yl)carbamate, 0.76 mL of acetic acid was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with 4.27 g of sodium triacetoxyborohydride, and stirred overnight. 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 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane=5:1] to obtain 2.96 g of tert-butyl (1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-piperidin-4-yl)carbamate.

출처