反応 #67979

反応方程式

sodium hydrogen carbonate

tert-butyl 4-amino-4-(hydroxymethyl)piperidine-1-carboxylate

2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

sodium triacetoxyborohydride

→

tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-(hydroxymethyl)piperidine-1-carboxylate

溶媒

acetic acid

dichloromethane

chloroform

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred at the same temperature for 2 hours
3. 3
   その他The organic layer was separated
4. 4
   抽出the aqueous layer was extracted with chloroform
5. 5
   洗浄the resultant solution was washed sequentially with water
6. 6
   乾燥an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
7. 7
   その他the solvent was removed under reduced pressure
8. 8
   その他The residue thus obtained
9. 9
   その他was purified by flash silica gel column chromatography [chloroform:gradient elution of methanol=100:0 to 80:20]

実験手順

To 10 mL of a dichloromethane solution containing 0.39 g of tert-butyl 4-amino-4-(hydroxymethyl)piperidine-1-carboxylate, 0.25 g of 2,3-dihydro-1,4-benzodioxin-6-carbaldehyde and 86 μL of acetic acid were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with 0.48 g of sodium triacetoxyborohydride, and stirred at the same temperature for 2 hours. Thereto were added chloroform and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resultant solution was washed sequentially with water and 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 flash silica gel column chromatography [chloroform:gradient elution of methanol=100:0 to 80:20] to obtain 91 mg of a colorless oily substance, tert-butyl 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-4-(hydroxymethyl)piperidine-1-carboxylate.

出典