反応 #10376

反応方程式

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

triethylamine

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

→

title compound

収率 69.8%

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

収率 69.8%

溶媒

acetonitrile

反応条件

後処理

1. 1
   濃縮The mixture is concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue dissolved in chloroform
3. 3
   洗浄washed with NaHCO3
4. 4
   乾燥brine, dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under vacuum
7. 7
   その他to afford a solid
8. 8
   その他The solid is purified by column chromatography (1:1:7 ethyl acetate/chloroform/hexanes)

実験手順

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).

出典