Methanol → (-)-cis-N-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-4-propionylbenzamide

反応式

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[N+:15]([O-])=O)=[CH:5][C:4]=1[O:18][CH3:19].[OH2:20].NN.[CH3:23][OH:24]>[Ni]>[CH3:19][O:18][C:4]1[CH:5]=[C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C:23](=[O:24])[C:3]2[CH:8]=[CH:7][C:6]([C:9](=[O:20])[CH2:10][CH3:11])=[CH:5][CH:4]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

実験手順

8.5 g of (+/−)-cis-1,2-dimethoxy-4-(2-nitrocyclohexyl)benzene are dissolved in 400 ml of methanol and treated at RT with 7 ml of hydrazine hydrate and 2.5 g of Raney nickel in portions in the course of 8 h. After stirring overnight at RT, the reaction mixture is filtered, the filtrate is concentrated and the residue is chromatographed on silica gel using a mixture of toluene/ethyl acetate/triethylamine=4/2/0.5. The title compound is obtained as an oil.