Reaktion #84718

Reaktionsgleichung

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

triethylamine

dioxane

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

→

title compound

Ausbeute 86.4%

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

Ausbeute 86.4%

Lösungsmittel

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   SonstigeThe organic layer was separated
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe resulting residue was purified by silica gel chromatography

Vorschrift

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.

Quelle