N-bromobutanimide → 6-Bromo-2,3-dihydro-1H-pyrrolizin-1-one
반응식
[C:1]1(=[O:9])[C:8]2[N:4]([CH:5]=[CH:6][CH:7]=2)[CH2:3][CH2:2]1.[Br:10]N1C(=O)CCC1=O>C1COCC1>[Br:10][C:6]1[CH:7]=[C:8]2[N:4]([CH2:3][CH2:2][C:1]2=[O:9])[CH:5]=1참가 물질
4
반응 조건
- 온도
- -10 °C
실험 절차
A mixture of 2,3-dihydro-1H-pyrrolizin-1-one (300 mg, 2.48 mmol) in THF (20 mL) was cooled to −10° C. in a brine bath. N-Bromosuccinimide (441 mg, 2.48 mmol) in THF (5 mL) was added dropwise, and the reaction mixture was stirred at −10° C. for 1 hour. The reaction was subsequently quenched with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were combined and dried and to give the title compound, which was used without further purification (520 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.02-3.05 (m, 2H), 4.17-4.20 (m, 2H), 6.58 (d, J=4.40 Hz, 1H), 6.67 (d, J=3.90 Hz, 1H). ESI-MS m/z [M+H]+ calc'd for C7H6BrNO, 200. found, 200.