Reaktion #88585

Reaktionsgleichung

(S)-tert-butyl pyrrolidin-3-ylcarbamate

pyridine

benzyl chloroformate

→

title compound

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

Lösungsmittel

methylene chloride

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to ambient temperature
2. 2
   workup.STIRRINGstirred for 4 hours
3. 3
   Sonstigethe organic layer was separated
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigepurified by flash chromatography (silica, 40 g, ISCO, 1-100% ethyl acetate in heptanes)

Vorschrift

A solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (4.2 g, 22 mmol) in methylene chloride (49 mL) was cooled at 0° C. and treated with pyridine (2.2 mL, 29 mmol) and benzyl chloroformate (3.8 mL, 29 mmol). The mixture was stirred at 0° C. for 30 minutes and then warmed to ambient temperature and stirred for 4 hours. The reaction mixture was diluted with water (100 mL) and methylene chloride (100 mL), the organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 40 g, ISCO, 1-100% ethyl acetate in heptanes) to afford the title compound as a white solid, which was used in the next step without any further purification (5.2 g, 73%).

Quelle