Reaktion #84697

Reaktionsgleichung

cis-tert-butyl 3-amino-4-(benzyloxycarbonylamino)piperidine-1-carboxylate

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

triethylamine

→

title compound

Ausbeute 83.0%

cis-tert-butyl 4-(benzyloxycarbonylamino)-3-((2-(trimethylsilyl)ethoxy)-carbonylamino)piperidine-1-carboxylate

Ausbeute 83.0%

Lösungsmittel

dioxane water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed by 1 M hydrochloric acid (50 mL), saturated sodium bicarbonate solution (50 mL) and brine (50 mL)
2. 2
   TrocknenThe organic layer was dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1)

Vorschrift

A solution of cis-tert-butyl 3-amino-4-(benzyloxycarbonylamino)piperidine-1-carboxylate (3.0 g, 8.6 mmol), 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate (2.5 g, 9.5 mmol) and triethylamine in dioxane/water (40 mL, v/v=1/1) was stirred at room temperature for 4 hours. After that, the solution was diluted with ethyl acetate (200 mL), and washed by 1 M hydrochloric acid (50 mL), saturated sodium bicarbonate solution (50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=4/1) to afford the title compound (3.5 g, 83%) as a white solid. MS (ES+) C24H39N3O6Si requires: 493, found: 516 [M+23]+.

Quelle