반응 #48284

반응 방정식

(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

용매

DCM

diethyl ether

반응 조건

후처리

1. 1
   기타quenched with sodium bicarbonate (sat, 100 mL)
2. 2
   기타The quenched reaction
3. 3
   workup.STIRRINGto stir for 2 h
4. 4
   추출the aq. layer was extracted with ether (3×75 mL)
5. 5
   세척The combined organics were washed with brine
6. 6
   건조dried with magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

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.

출처