반응 #48681

반응 방정식

pyridine sulfur trioxide

(2R,3S,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethyl-3-methylmorpholine-4-carboxylic acid tert-butyl ester

N,N-diisopropylethylamine

→

title compound

수율 99.7%

(2R,3S,5R)-2-(2,2-Dimethylpropoxy)-5-formyl-3-methylmorpholine-4-carboxylic acid tert-butyl ester

수율 99.7%

용매

dichloromethane

dimethylsulfoxide

반응 조건

후처리

1. 1
   workup.STIRRINGstir 30 minutes
2. 2
   workup.ADDITIONPour into ice-cold saturated aqueous sodium chloride
3. 3
   추출extract with ethyl acetate
4. 4
   세척Wash the ethyl acetate layer with 1 N aqueous citric acid, saturated aqueous sodium chloride),
5. 5
   건조dry (magnesium sulfate)
6. 6
   여과filter
7. 7
   농축concentrate

실험 절차

Add pyridine sulfur trioxide complex (0.42 g) to (2R,3S,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethyl-3-methylmorpholine-4-carboxylic acid tert-butyl ester (0.46 g, 1.45 mmol) and N,N-diisopropylethylamine (0.66 g, 5.07 mmol) in dichloromethane (1 mL) and dimethylsulfoxide (4 mL) at −2° C. and stir 30 minutes. TLC shows some alcohol remaining. Add more pyridine sulfur trioxide (100 mg) and stir 30 minutes. Pour into ice-cold saturated aqueous sodium chloride and extract with ethyl acetate. Wash the ethyl acetate layer with 1 N aqueous citric acid, saturated aqueous sodium chloride), dry (magnesium sulfate), filter and concentrate to give the title compound as an oil (456 mg).

출처