反応 #84718

反応方程式

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

triethylamine

dioxane

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

→

title compound

収率 86.4%

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

収率 86.4%

溶媒

water

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with brine
2. 2
   その他The organic layer was separated
3. 3
   濃縮concentrated
4. 4
   その他The resulting residue was purified by silica gel chromatography

実験手順

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.

出典