Реакция #67979

Уравнение реакции

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

Растворители

acetic acid

dichloromethane

chloroform

Условия реакции

Обработка

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

Методика

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.

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