تفاعل #10378

معادلة التفاعل

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

triethylamine

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

→

title compound

المردود 63.6%

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

المردود 63.6%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent is removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in chloroform
3. 3
   غسيلwashed with NaHCO3
4. 4
   تجفيفbrine, dried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىto afford a solid
8. 8
   أخرىThe solid is then purified by column chromatography (1:1:6 ethyl acetate/chloroform/hexanes)

الإجراء التجريبي

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).

المصدر