反応 #48284

反応方程式

(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

溶媒

DCM

diethyl ether

反応条件

後処理

1. 1
   その他quenched with sodium bicarbonate (sat, 100 mL)
2. 2
   その他The quenched reaction
3. 3
   workup.STIRRINGto stir for 2 h
4. 4
   抽出the aq. layer was extracted with ether (3×75 mL)
5. 5
   洗浄The combined organics were washed with brine
6. 6
   乾燥dried with magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated

実験手順

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.

出典