2-((1-Naphthalenyloxy)methyl)oxirane → N-(6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-naphthyloxy)propanamine
Reaktionsgleichung
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH2:3]1.[C:13]1([O:23][CH2:24][CH:25]2[O:27][CH2:26]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>C(O)C>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH2:3][CH:2]([NH:1][CH2:26][CH:25]([OH:27])[CH2:24][O:23][C:13]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=1)[CH2:11][CH2:10]2Komponenten
4
Versuchsvorschrift
A solution of 2-amino-6-hydroxytetralin (2.6 g) and 1-naphthyloxy-2,3-epoxypropane (3.2 g) in ethanol (80 ml) is refluxed for 5 hours, and then allowed to cool to room temperature. The solvent is evaporated off under reduced pressure and the thus obtained oil is chromatographed on a silica gel column eluting first with ethyl acetate up to complete elution of the first spot, and then with a mixture ethyl acetate/reethanol 9/1 v/v up to complete elution of the product. The fractions are pooled and concentrated under reduced pressure. The residue is dissolved in isopropanol (20 ml) and a solution of fumaric acid (0.95 g) in isopropanol (10 ml) is then added thereto. The precipitate is recovered by filtration, washed with ethyl ether and dissolved in water. A concentrated sodium hydroxide solution is then added thereto up to a basic pH and the solution is extracted with ethyl acetate. The organic extract is dried over sodium sulfate and concentrated to dryness. The residue is triturated with a small amount of ethyl acetate and filtered yielding 1.9 g of N-(6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(1-naphthyloxy)propanamine; m.p. 118°-120° C.