Dimethylamine → [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester
反応式
[C:1]([O:5][C:6]([N:8]([CH3:25])[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][NH:27][CH3:28]>CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][N:27]([CH3:28])[CH3:26])=[CH:11][CH:10]=1)[CH3:25])([CH3:4])([CH3:3])[CH3:2]参加物
4
実験手順
A solution of 1.84 g (5 mmol) of Methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-pent-4-ynyl ester in 20 ml DMA was treated with 8.93 ml (50 mmol) of (33% in ethanol, 5.6 M) dimethylamine and stirred at RT for 18 h. The reaction was treated again with 4.46 ml (2 mmol) (25 mmol) of (33% in ethanol, 5.6 M) dimethylamine and stirred at RT for further 6 h. The solution was concentrated and the residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution, dried (Na2SO4) and evaporated to yield 1.50 g (95%) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester, MS: 317 (MH+).