[2-(6-nitro-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester → [2-(6-amino-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
반응식
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([N+:19]([O-])=O)=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[NH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]참가 물질
4
실험 절차
A mixture of [2-(6-nitro-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (5 g, 16.4 mmol) and Raney Ni (1 g) in EtOH (100 mL) was stirred at room temperature under H2 (1 atm) for 5 h. Raney Ni was filtered off and the filtrate was evaporated under reduced pressure. The crude product was purified by column chromatography to give [2-(6-amino-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (B-10) (3 g, 67%). 1H NMR (DMSO-d6) δ 10.1 (br s, 1 H), 7.11 (d,J=8.4 Hz, 1 H), 6.77-6.73 (m, 2 H), 6.46 (d,J=1.5 Hz, 1 H), 6.32 (dd,J=8.4, 2.1 Hz, 1 H), 4.62 (s, 2 H), 3.14-3.08 (m, 2 H), 2.67-2.62 (m, 2 H), 1.35 (s, 9H); ESI-MS 275.8 m/z (MH+).