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Sodium hydride → 2,3-dibenzyl 3-tert-butyl 1-cyclopropyl-2(R),3(R,S),3-propane-tricarboxylate

HRID 1108326
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1108326
[C:1]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[CH:21]1([CH2:24][C@@H:25](OS(C(F)(F)F)(=O)=O)[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:23][CH2:22]1>COCCOC.ClCCl>[CH:21]1([CH2:24][C@@H:25]([C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH:2]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:1]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:22][CH2:23]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 2736712Benzyl tert-butyl malonateHCID 22870963benzyl 3-cyclopropyl-2(R)-trifluoromethylsulphonyloxypropionate

Produkt 1

HCID 1317218122,3-dibenzyl 3-tert-butyl 1-cyclopropyl-2(R),3(R,S),3-propane-tricarboxylateAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 3.8 g of benzyl tert-butyl malonate in 50 ml of 1,2-dimethoxyethane was treated with 0.504 g of an 80% dispersion of sodium hydride in mineral oil. The mixture was stirred at room temperature for 30 minutes and then cooled to 0°. A solution of 5.37 g of benzyl 3-cyclopropyl-2(R)-trifluoromethylsulphonyloxypropionate in 20 ml of dichloromethane was added dropwise at 0°. The mixture was stirred at 0° for 2 hours and then left to warm to room temperature overnight. The solvent was evaporated and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate the solvent was evaporated to give 6.54 g of 2,3-dibenzyl 3-tert-butyl 1-cyclopropyl-2(R),3(R,S),3-propane-tricarboxylate as a 1:1 mixture of diastereoisomers in the form of an orange oil.

Aufarbeitung

  1. temperaturecooled to 0°
  2. stirringThe mixture was stirred at 0° for 2 hours
  3. waitleft
  4. temperatureto warm to room temperature overnight
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe solution was washed with water and saturated sodium chloride solution
  8. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  9. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-bb4cb048897f4ddbaf3716626d1af6c4
Quelldatensatz
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06066662

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