Reaktion #10380

Reaktionsgleichung

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

pyrrolidin-3-ylcarbamic acid tert-butyl ester

triethylamine

→

title compound

Ausbeute 77.6%

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

Ausbeute 77.6%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe yellow solution is concentrated
2. 2
   workup.ADDITIONpoured into saturated NaHCO3 solution
3. 3
   Extraktionextracted with dichloromethane
4. 4
   WaschenThe combined organic extracts are washed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under vacuum
8. 8
   SonstigeThe resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes)

Vorschrift

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+).

Quelle