反応 #67997

反応方程式

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

収率 64.3%

溶媒

acetic acid

chloroform

反応条件

後処理

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

実験手順

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.

出典