Methyl 2-(3-((benzylamino)methyl)-6-nitro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acetate → 2-((Benzylamino)methyl)-2,3-dihydro-7H-[1,4]dioxino[2,3-e]indol-8(9H)-one
反応式
[CH2:1]([NH:8][CH2:9][CH:10]1[CH2:15][O:14][C:13]2[CH:16]=[CH:17][C:18]([N+:25]([O-])=O)=[C:19]([CH2:20][C:21](OC)=[O:22])[C:12]=2[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)C>[CH2:1]([NH:8][CH2:9][CH:10]1[O:11][C:12]2=[C:19]3[C:18](=[CH:17][CH:16]=[C:13]2[O:14][CH2:15]1)[NH:25][C:21](=[O:22])[CH2:20]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1参加物
3
反応条件
- 温度
- 70 °C
実験手順
The methyl ester from Example 5 (43 mg) was dissolved in 1:1 ethyl acetate/ethanol (10 mL) and filtered through a syringe filter to remove insoluble material. Platinum oxide (35 weight percent) was added and the mixture placed under 50 psi of hydrogen gas on a Parr shaker overnight. TLC analysis with 95:5 CH2Cl2/MeOH showed consumption of starting material with a more polar product having been formed. The mixture was filtered through a 0.5 μm syringe filter, washing with 1:1 EtOAc/EtOH, and the filtrate concentrated under reduced pressure to a pale red-brown glass. The crude material was redissolved in ethanol (20 mL) and 20 μL of concentrated HCl were added. The solution was warmed to 70° C. and allowed to stir overnight. TLC of the reaction mixture (96:4 CH2Cl2/MeOH) showed the formation of a new product with no remaining starting material. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to a light orange film. This was chromatographed over silica gel eluting with 96:4 CH2Cl2/MeOH. The title product was isolated in 22% yield.