反応 #10382

反応方程式

2,3,4-trifluorobenzoic acid ethyl ester

pyrrolidin-3-ylcarbamic acid tert-butyl ester

triethylamine

→

title compound

収率 70.1%

4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,3-difluorobenzoic acid ethyl ester

収率 70.1%

溶媒

acetonitrile

反応条件

後処理

1. 1
   濃縮The solution is concentrated in vacuo
2. 2
   workup.ADDITIONpoured into a saturated NaHCO3 solution
3. 3
   抽出The mixture is then extracted with chloroform
4. 4
   洗浄the combined organic extracts are washed with brine
5. 5
   乾燥dried with Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮the mixture concentrated in vacuo
8. 8
   その他The resulting residue is then purified by column chromatography (1:7 ethyl acetate/hexanes)

実験手順

A solution of 2,3,4-trifluorobenzoic acid ethyl ester (Example 1g, 3.70 g, 18.1 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (4.02 g, 21.6 mmol), and triethylamine (18.0 mL, 129 mmol) in acetonitrile (50 mL) is heated at 50° C. under nitrogen atmosphere for 4.5 hours. The solution is concentrated in vacuo and poured into a saturated NaHCO3 solution. The mixture is then extracted with chloroform, and the combined organic extracts are washed with brine, dried with Na2SO4, filtered, and the mixture concentrated in vacuo. The resulting residue is then purified by column chromatography (1:7 ethyl acetate/hexanes) to afford the title compound (4.70 g). 1H NMR (CDCl3): δ 7.59–7.49 (m, 1H), 6.35–6.26 (m, 1H), 4.88–4.84 (bd, 1H), 4.39–4.28 (m, 3H), 3.81–3.50 (m, 3H), 3.48–3.34 (m, 1H), 2.32–2.15 (m, 1H), 2.02–1.76 (m, 1H), 1.45 (s, 9H), 1.40 (t, 3H).

出典