반응 #88586

반응 방정식

(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

용매

water

methylene chloride

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   건조dried over sodium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타purified flash chromatography (silica, 40 g, ISCO, 1-20% methanol in methylene chloride)

실험 절차

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%).

출처