Reacción #10378

Ecuación de reacción

2,3,4,5,6-pentafluorobenzoic acid benzyl ester

triethylamine

(S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester

→

title compound

Rendimiento 63.6%

4-[(S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,3,5,6-tetrafluorobenzoic acid benzyl ester

Rendimiento 63.6%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent is removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in chloroform
3. 3
   Lavadowashed with NaHCO3
4. 4
   Secadobrine, dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otroto afford a solid
8. 8
   OtroThe solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes)

Procedimiento

A solution of 2,3,4,5,6-pentafluorobenzoic acid benzyl ester (Example 1d, 8.05 g, 26.6 mmol), triethylamine (26 mL, 186 mmol), and (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (5.6 g, 30 mmol) in acetonitrile (150 mL) is stirred at room temperature for 24 hours. The solvent is removed under vacuum and the residue dissolved in chloroform, washed with NaHCO3 and then brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford a solid. The solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes) to yield the title compound as a solid (7.92 g). 1H NMR (CDCl3): δ 7.48–7.30 (m, 5H), 5.35 (s, 2H), 4.77–4.50 (m, 1H), 4.37–4.19 (m, 1H), 4.01–3.63 (m, 3H), 3.59–3.46 (m, 1H), 2.29–2.09 (m, 1H), 2.01–1.82 (m, 1H), 1.45 (s, 9H).

Fuente