Reaktion #84687

Reaktionsgleichung

2-((1S,2R,3S,5S)-3-aminobicyclo[3.1.0]hexan-2-yl)isoindoline-1,3-dione

2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

triethylamine

→

title compound

Ausbeute 78.3%

2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate

Ausbeute 78.3%

Lösungsmittel

dioxane water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed by 1 M hydrochloric acid (2×50 mL), saturated sodium bicarbonate solution (2×50 mL) and brine (50 mL)
2. 2
   EinengenThe organic layer was concentrated under reduced pressure
3. 3
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4)

Vorschrift

A solution of 2-((1S,2R,3S,5S)-3-aminobicyclo[3.1.0]hexan-2-yl)isoindoline-1,3-dione (2.0 g, 8.264 mmol), 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate (3.2 g, 12.396 mmol) and triethylamine (3.4 mL, 24.792 mmol) in dioxane/water (100 mL, v/v=1/1) was stirred at room temperature for 1.5 hours. The reaction mixture was then diluted with ethyl acetate (100 mL), washed by 1 M hydrochloric acid (2×50 mL), saturated sodium bicarbonate solution (2×50 mL) and brine (50 mL). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4) to afford the title compound (2.5 g, 78%) as a yellow oil. MS (ES+) C20H26N2O4Si requires: 386, found: 410 [M+23]+.

Quelle