反応 #10380

反応方程式

2,4,5-trifluoro-3-methoxybenzoic acid ethyl ester

pyrrolidin-3-ylcarbamic acid tert-butyl ester

triethylamine

→

title compound

収率 77.6%

4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,5-difluoro-3-methoxybenzoic acid ethyl ester

収率 77.6%

溶媒

acetonitrile

反応条件

後処理

1. 1
   濃縮The yellow solution is concentrated
2. 2
   workup.ADDITIONpoured into saturated NaHCO3 solution
3. 3
   抽出extracted with dichloromethane
4. 4
   洗浄The combined organic extracts are washed with brine
5. 5
   乾燥dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under vacuum
8. 8
   その他The resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes)

実験手順

A solution of 2,4,5-trifluoro-3-methoxybenzoic acid ethyl ester (Example 1f, 2.821 g, 12.05 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (3.310 g, 17.77 mmol), and triethylamine (9.13 g, 12.6 mL, 90.23 mmol) in acetonitrile (50 mL) is heated at 40° C. under nitrogen for 2 days. The yellow solution is concentrated to near dryness and poured into saturated NaHCO3 solution and extracted with dichloromethane. The combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum. The resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes) to afford the title compound as a yellow solid (3.743 g). MS EI: m/z 401 (MH+).

出典