Reaktion #84713

Reaktionsgleichung

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

triethylamine

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

→

title compound

Ausbeute 52.0%

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

Ausbeute 52.0%

Lösungsmittel

ethyl acetate

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   EinengenThe organic layer was concentrated
3. 3
   Sonstigepurification by silica gel column with petroleum ether/ethyl acetate=4/1 to 1/1

Vorschrift

To a solution of (4R,5R)-5-amino-2,2-dimethyl-tetrahydro-2H-pyran-4-ol (550 mg, 2.40 mmol) and triethylamine (484 mg, 4.80 mmol) in dioxane (5 mL) and water (5 mL) was added 2-(trimethylsilyl)ethyl 2,5-dioxopyrrolidine-1-carboxylate (750 mg, 2.90 mmol) at room temperature. 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 concentrated, and the residue was purification by silica gel column with petroleum ether/ethyl acetate=4/1 to 1/1 to afford the title compound (360 mg, 52% for 2 steps) as a gray solid.

Quelle