反应 #84718

反应方程式

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

triethylamine

dioxane

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

→

title compound

收率 86.4%

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

收率 86.4%

溶剂

water

ethyl acetate

反应条件

后处理

1. 1
   洗涤washed with brine
2. 2
   其他The organic layer was separated
3. 3
   浓缩concentrated
4. 4
   其他The resulting residue was purified by silica gel chromatography

实验过程

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.

来源