反应 #84689

反应方程式

ammonium chloride

(S)-methyl 2-(tert-butoxycarbonylamino)-4-(methylsulfonyl)butanoate

potassium bis(trimethylsilyl)amide

→

title compound

tert-butyl (1,1-dioxido-3-oxotetrahydro-2H-thiopyran-4-yl)carbamate

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   其他The reaction mixture was subjected to liquid separation
4. 4
   洗涤The resultant organic layer was then washed with water and brine
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   其他The solvent was removed under reduced pressure
7. 7
   过滤the formed solid was collected by filtration

实验过程

A solution of (S)-methyl 2-(tert-butoxycarbonylamino)-4-(methylsulfonyl)butanoate (2 g, 6.78 mmol) in tetrahydrofuran (50 mL) was cooled to −78° C., to which potassium bis(trimethylsilyl)amide (1.0 M, toluene solution, 15 ml) was added dropwise, and the mixture was stirred at −78° C. for 2 hours and at room temperature for another 2 hours. An aqueous solution of ammonium chloride (1 M) was added, and the mixture was stirred. The reaction mixture was subjected to liquid separation. The resultant organic layer was then washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the formed solid was collected by filtration to obtain the title compound. The water layer separated previously was extracted twice with ethyl acetate. The resultant organic layers were combined, washed with water and brine, and dried over anhydrous magnesium sulfate. The ethyl acetate extracts were combined, dried and then concentrated under reduced pressure to obtain the title compound. The combined product was purified by flash column chromatography (ethyl acetate:petroleum ether, 3:1) to afford the title compound (55 mg, yield 22%) as a yellow solid.

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