Reaktion #48284

Reaktionsgleichung

(S)—N-((2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide

SODIUM BICARBONATE

SODIUM THIOSULFATE

Dess-MartinPeriodinane

→

solid/oil

(S)—N-((2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide

Lösungsmittel

DCM

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with sodium bicarbonate (sat, 100 mL)
2. 2
   SonstigeThe quenched reaction
3. 3
   workup.STIRRINGto stir for 2 h
4. 4
   Extraktionthe aq. layer was extracted with ether (3×75 mL)
5. 5
   WaschenThe combined organics were washed with brine
6. 6
   Trocknendried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

To a 250 ml rbf was added (S)—N-((2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (160.00 mg) and DCM (10 ml) followed by SODIUM BICARBONATE (148.7 mg, 5 eq) and Dess-MartinPeriodinane (195.1 mg, 1.30 eq). The reaction was allowed to stir for 2 h and then quenched with sodium bicarbonate (sat, 100 mL) and added SODIUM THIOSULFATE (391.7 mg, 2477 μmol) along with diethyl ether (100 ml). The quenched reaction was allowed to stir for 2 h and then the aq. layer was extracted with ether (3×75 mL). The combined organics were washed with brine and dried with magnesium sulfate, filtered and concentrated to give 1280 mg of a solid/oil mixture, which was purified on a silica gel column (20% EtOAc in hexanes) to give the title compound as a colorless oil.

Quelle