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(2R,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester → (3R)-1-t-Butoxycarbonyl-3-t-butyldimethylsilyloxy-L-proline

HRID 1780279
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1780279
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][C@@H:25]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[C@H:22]1[CH2:23][OH:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CC(C)=O.O>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][C@@H:25]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[C@H:22]1[C:23]([OH:3])=[O:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]
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Komponenten

5

Edukt 2

HCID 11012982(2R,3R)-3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl esterHCID 131709961Jones' reagent

Produkt 1

HCID 54215964(3R)-1-t-Butoxycarbonyl-3-t-butyldimethylsilyloxy-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.7 ml of Jones' reagent (chromium trioxide/4N aqueous sulfuric acid: Bowden, Heibron, Jones & Weedon, J. Chem. Soc., 1946, 39) was added, whilst ice-cooling, to a solution of 245 mg (0.74 mmol) of (3R)-1-t-butoxycarbonyl-3-t-butyldimethylsilyloxy-L-prolinol [prepared as described in step (a) above] in 10 ml of acetone, and the mixture was stirred at 0° C. for 2 hours. At the end of this time, the reaction mixture was diluted with water and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was triturated with hexane, to give 191 mg of the title compound as colorless crystals, melting at 146°-147° C.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe residue was triturated with hexane

Quellen und Nachweise

ORD-Eintrag
ord-2c9a389ba50e4b619b8252e2e56b8277
Quelldatensatz
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05629406

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