반응 #49157

반응 방정식

N-Boc-L-proline

ethyl 3-(4-bromophenyl)-3-oxopropanoate

NBS

Hunig's base

Ethyl 2-bromo-3-(4-bromophenyl)-3-oxopropanoate

→

(2S)-2-(1-(4-bromophenyl)-3-ethoxy-1,3-dioxopropan-2-yl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate

용매

acetonitrile

CH2Cl2

반응 조건

후처리

1. 1
   세척The reaction mixture was washed with NaHCO3 solution, brine
2. 2
   건조dried (MgSO4)
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to give a residue which
6. 6
   기타was not purified
7. 7
   workup.STIRRINGthe solution stirred 18 hr
8. 8
   기타The solvent was removed by rotary evaporation
9. 9
   세척washed with 0.1 N HCl, and brine

실험 절차

The ethyl 3-(4-bromophenyl)-3-oxopropanoate (15 g, 55 mmol) was dissolved in CH2Cl2 (600 mL) and freshly recrystallized NBS (9.8 g, 55 mmol) was added and the solution stirred 18 hr. The reaction mixture was washed with NaHCO3 solution, brine, and dried (MgSO4), filtered, and concentrated to give a residue which was not purified. Ethyl 2-bromo-3-(4-bromophenyl)-3-oxopropanoate (16.5 g, 48 mmol) and N-Boc-L-proline (10 g, 48 mmol) were taken up in acetonitrile (450 mL) and Hunig's base (16 mL, 95 mmol) was added and the solution stirred 18 hr. The solvent was removed by rotary evaporation and the residue taken up in ethyl acetate, washed with 0.1 N HCl, and brine. 1H NMR (300 MHz, DMSO-d6) δ 7.95 (d, J=8.4 Hz, 2H), 7.79 (d, J=8.4 Hz, 2H), 6.68-6.65 (m, 1H), 4.39-4.30 (m, 1H), 4.21-4.12 (m, 2H), 2.27-2.21 (m, 1H), 2.0-1.95 (m, 1H), 1.90-1.76 (m, 2H), 1.39 (s, 2H), 1.31 (s, 9H), 1.11 (t, J=7.3 Hz, 3H).

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