반응 #48685

반응 방정식

(2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

N,N-diisopropylethylamine

→

desired compound

(2R,5R)-2-(2,2-Dimethylpropoxy)-5-formylmorpholine-4-carboxylic acid tert-butyl ester

용매

dimethylsulfoxide

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONpour into ice cold saturated aqueous sodium chloride
2. 2
   추출Extract with 10% ethyl acetate/hexanes
3. 3
   세척Wash with 0.1 N aqueous citric-acid and saturated aqueous sodium chloride
4. 4
   건조Dry (magnesium sulfate)
5. 5
   여과filter
6. 6
   농축concentrate

실험 절차

Add pyridine sulfur trioxide complex (4.82 g, 30.26 mmol) to (2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (5.10 g, 16.81 mmol) and N,N-diisopropylethylamine (7.61 g, 58.83 mmol) in dimethylsulfoxide (42 mL) and dichloromethane (8 mL) at −4° C. Stir 20 minutes, pour into ice cold saturated aqueous sodium chloride. Extract with 10% ethyl acetate/hexanes. Wash with 0.1 N aqueous citric-acid and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate to give the desired compound of a colorless oil, which is used directly in the next step without further purification (5.02 g).

출처