반응 #10376

반응 방정식

2,3,4,6-tetrafluorobenzoic acid ethyl ester

triethylamine

(S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester

→

title compound

수율 69.8%

4-[(S)-3-tert-Butoxycarbonylaminopyrrolodin-1-yl]-2,3,6-trifluorobenzoic acid ethyl ester

수율 69.8%

용매

acetonitrile

반응 조건

후처리

1. 1
   농축The mixture is concentrated in vacuo
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 under vacuum
7. 7
   기타to afford a solid
8. 8
   기타The solid is purified by column chromatography (1:1:7 ethyl acetate/chloroform/hexanes)

실험 절차

A solution of 2,3,4,6-tetrafluorobenzoic acid ethyl ester (Example 1b, 5.1 g, 22.9 mmol), triethylamine (22 mL, 157 mmol), and (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (5.2 g, 27.9 mmol) in acetonitrile (60 mL) is stirred at room temperature for 64 hours. The mixture is concentrated in vacuo and the residue dissolved in chloroform, washed with NaHCO3 and then brine, dried over Na2SO4, filtered, and concentrated under vacuum to afford a solid. The solid is purified by column chromatography (1:1:7 ethyl acetate/chloroform/hexanes) to afford the title compound (6.21 g). 1H NMR (CDCl3): δ 6.07 (ddd, 1H), 4.78–4.63 (bd, 1H), 4.49–4.22 (m, 3H), 3.80–3.68 (m, 1H), 3.66–3.28 (m, 3H), 2.33–2.13 (m, 1H), 2.04–1.83 (m, 1H), 1.45 (s, 9H), 1.36 (t, 3H).

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