تفاعل #49157

معادلة التفاعل

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

المذيبات

acetonitrile

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   غسيلThe reaction mixture was washed with NaHCO3 solution, brine
2. 2
   تجفيفdried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىto give a residue which
6. 6
   أخرىwas not purified
7. 7
   workup.STIRRINGthe solution stirred 18 hr
8. 8
   أخرىThe solvent was removed by rotary evaporation
9. 9
   غسيلwashed with 0.1 N HCl, and brine

الإجراء التجريبي

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).

المصدر