Reacción #67979

Ecuación de reacción

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

Disolventes

acetic acid

dichloromethane

chloroform

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente