Reaktion #88586

Reaktionsgleichung

(S)-benzyl 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate

3-fluoropropyl trifluoromethanesulfonate

sodium hydride

→

title compound

(S)-benzyl 3-(tert-butoxycarbonyl(3-fluoropropyl)amino)pyrrolidine-1-carboxylate

Lösungsmittel

water

methylene chloride

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Trocknendried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigepurified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride)

Vorschrift

To a mixture of (S)-benzyl 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate (400 mg, 1.2 mmol) and 3-fluoropropyl trifluoromethanesulfonate (433 mg, 2.1 mmol) in tetrahydrofuran (10 mL) was added sodium hydride as 60% dispersion in mineral oil (146 mg, 3.6 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and then diluted with water (20 mL) and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as a colorless oil, which was used in the next step without any further purification (475 mg, 100%).

Quelle