1-(Benzyloxycarbonyl)-4-[(4-nitrophenoxy)methyl]piperidine → 4-[(4-Aminophenoxy)methyl]-1-(benzyloxycarbonyl)piperidine

反応式

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.Cl.[Zn]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:16][CH2:15]2)=[CH:24][CH:23]=1

参加物

実験手順

A solution of the product of part (ii) (10.0 g) in ethanol (400 ml) and 2N hydrochloric acid (200 ml) was heated to reflux with stirring. Zinc dust (8.80 g) was added at such a rate that the ensuing reaction was not too vigorous. The mixture was heated under reflux for 0.25 hour and then cooled and filtered. The filtrate was made basic with 0.88 ammonia solution and diluted with a large volume of water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel, eluting with dichloromethane. Earlier fractions contained impurity and the pure product was eluted in the later fractions. The product fractions were combined and evaporated to give an oil, (5.50 g). The product darkened rapidly and was used directly without further purification.