Reacción #48284

Ecuación de reacción

(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

Disolventes

DCM

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with sodium bicarbonate (sat, 100 mL)
2. 2
   OtroThe quenched reaction
3. 3
   workup.STIRRINGto stir for 2 h
4. 4
   Extracciónthe aq. layer was extracted with ether (3×75 mL)
5. 5
   LavadoThe combined organics were washed with brine
6. 6
   Secadodried with magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

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.

Fuente