반응 #10378

반응 방정식

2,3,4,5,6-pentafluorobenzoic acid benzyl ester

triethylamine

(S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester

→

title compound

수율 63.6%

4-[(S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,3,5,6-tetrafluorobenzoic acid benzyl ester

수율 63.6%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The solvent is removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in chloroform
3. 3
   세척washed with NaHCO3
4. 4
   건조brine, dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to afford a solid
8. 8
   기타The solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes)

실험 절차

A solution of 2,3,4,5,6-pentafluorobenzoic acid benzyl ester (Example 1d, 8.05 g, 26.6 mmol), triethylamine (26 mL, 186 mmol), and (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (5.6 g, 30 mmol) in acetonitrile (150 mL) is stirred at room temperature for 24 hours. The solvent is removed under vacuum and the residue dissolved in chloroform, washed with NaHCO3 and then brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford a solid. The solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes) to yield the title compound as a solid (7.92 g). 1H NMR (CDCl3): δ 7.48–7.30 (m, 5H), 5.35 (s, 2H), 4.77–4.50 (m, 1H), 4.37–4.19 (m, 1H), 4.01–3.63 (m, 3H), 3.59–3.46 (m, 1H), 2.29–2.09 (m, 1H), 2.01–1.82 (m, 1H), 1.45 (s, 9H).

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