반응식
[CH2:1]([N:8]([CH2:20]/[C:21](/[CH3:24])=[CH:22]/[CH3:23])[C:9]([CH:11]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>BrC1C=CC=CC=1>[CH2:1]([N:8]1[C:9](=[O:10])[C@H:11]2[C@@:21]([CH3:24])([C@@H:22]([CH3:23])[CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=32)[CH2:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1참가 물질
반응 조건
- 온도
- 190 °C
실험 절차
(E)-N-Benzyl-3-chloro-N-(2-methylbut-2-enyl)-1,2-dihydrocyclobutabenzene-1-carboxamide (0.971 mmol, 330 mg) was dissolved in bromobenzene (6 ml) and heated in a microwave reactor at 190° C. for 1 hour. The solvent was removed in vacuo and the resulting residue was purified by silica column chromatography (eluting with heptane then 5-20% ethyl acetate in heptane) to give (3aR*,4S*,9bR*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one (229 mg) 1H NMR (400 MHz, CDCl3) ppm 7.42 (1H, d, ArH), 7.33-7.22 (7H, m, ArH), 4.57 (1H, d, CHHPh), 4.34 (1H, d, CHHPh), 3.34 (1H, s, CH), 3.24 (1H, d, CH), 3.01 (1H, d, CH), 2.90 (1H, dd, CH), 2.38 (1H, dd, CH), 1.77 (1H, m, CH), 1.04 (3H, s, CH3), 0.91 (3H, d, CH3) and (3aR*,4S*,9bS*)-2-benzyl-6-chloro-3a,4-dimethyl-2,3,3a,4,5,9b-hexahydro-H-benzo[e]isoindol-1-one (96 mg) 1H NMR (400 MHz, CDCl3) ppm 8.36 (1H, d, ArH), 7.45-7.13 (7H, m, 7×ArH), 4.55 (1H, d, CHHPh), 4.47 (1H, d, CHHPh), 3.40 (1H, s, CH), 3.07-2.94 (3H, m, 3×CH), 2.40 (1H, dd, CH), 2.21-2.10 (1H, m, CH2), 0.99 (3H, d, CH3), 0.68 (3H, s, CH3).
후처리
- customThe solvent was removed in vacuo
- customthe resulting residue was purified by silica column chromatography (
- washeluting with heptane
출처 및 근거
- ORD 기록
- ord-b52eaa6b25244f6eb3e619c93ddee907
- 출처 데이터셋
- uspto-grants-2014_05
- 특허 번호
- US08729274B2
연결된 노트
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