반응 #84718

반응 방정식

(4S,5S)-5-amino-2,2-dimethyl-tetrahydro-2H-pyran-4-ol

triethylamine

dioxane

2-(trimethylsilyl)ethyl 2,5-dioxopyrrolidine-1-carboxylate

→

title compound

수율 86.4%

2-(trimethylsilyl)ethyl (3S,4S)-4-hydroxy-6,6-dimethyl-tetrahydro-2H-pyran-3-ylcarbamate

수율 86.4%

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   세척washed with brine
2. 2
   기타The organic layer was separated
3. 3
   농축concentrated
4. 4
   기타The resulting residue was purified by silica gel chromatography

실험 절차

To a solution of (4S,5S)-5-amino-2,2-dimethyl-tetrahydro-2H-pyran-4-ol (1.1 g, 4.0 mmol) and triethylamine (1.1 mL, 8.0 mmol) in a mixed solvent of dioxane (5 mL) and water (5 mL) at room temperature was added 2-(trimethylsilyl)ethyl 2,5-dioxopyrrolidine-1-carboxylate (1.2 g, 4.8 mmol). The reaction mixture was stirred at room temperature for 4 hours. After that, the solution was diluted with ethyl acetate and washed with brine. The organic layer was separated and concentrated. The resulting residue was purified by silica gel chromatography using petroleum ether/ethyl acetate=4/1 to 1/1 as the eluent to afford the title compound (1.0 g, 86% for 2 steps) as a yellow oil.

출처