Reaction #48284

Reaction equation

(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

Solvents

DCM

diethyl ether

Conditions

Workup

1. 1
   Otherquenched with sodium bicarbonate (sat, 100 mL)
2. 2
   OtherThe quenched reaction
3. 3
   workup.STIRRINGto stir for 2 h
4. 4
   Extractionthe aq. layer was extracted with ether (3×75 mL)
5. 5
   WashThe combined organics were washed with brine
6. 6
   Dryingdried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

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.

Source