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

HRID 20403

Reaktionsgleichung

Reaktionsgleichung von HRID 20403
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 58972240(2R,3S,5R)-2-(2,2-Dimethylpropoxy)-5-formyl-3-methylmorpholine-4-carboxylic acid tert-butyl esterAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3e48c768ad554b59a51e4f94284c503d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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