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

HRID 20403

반응식

HRID 20403 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][OH:15])[CH2:12][O:11][C@@H:10]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C@@H:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.S(=O)(=O)=O.N1C=CC=CC=1>ClCCl.CS(C)=O>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C@@H:10]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C@@H:9]1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridineHCID 68563537(2R,3S,5S)-2-(2,2-Dimethylpropoxy)-5-hydroxymethyl-3-methylmorpholine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 58972240(2R,3S,5R)-2-(2,2-Dimethylpropoxy)-5-formyl-3-methylmorpholine-4-carboxylic acid tert-butyl ester수율 99.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

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).

후처리

  1. stirringstir 30 minutes
  2. additionPour into ice-cold saturated aqueous sodium chloride
  3. extractionextract with ethyl acetate
  4. washWash the ethyl acetate layer with 1 N aqueous citric acid, saturated aqueous sodium chloride),
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate

출처 및 근거

ORD 기록
ord-3e48c768ad554b59a51e4f94284c503d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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