Borane;tetrahydrofuran → N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline
Reaktionsgleichung
B.C1COCC1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH3:30])[CH:25]=3)[CH:20]2[CH3:31])=O)=[CH:12][CH:11]=1)([O-:9])=[O:8]>Cl>[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][CH3:30])[CH:25]=3)[CH:20]2[CH3:31])=[CH:12][CH:11]=1)([O-:9])=[O:8]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A stirred solution of 200 ml of 0.5 M borane/THF was treated with N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline (11.5 g, 0.03 m) portionwise, at room temperature, then warmed to reflux. After 30 min at reflux, the reaction was cooled and acidified with 60 ml of 20% HCl, added dropwise. The acidified reaction mixture was refluxed one hour, then concentrated on the rotovap at 40° C. to about 1/3 volume, then diluted with 600 ml water. The mixture was basified, then extracted with CH2Cl2 (2×400 ml). The CH2Cl2 was concentrated to an oil which crystallized when treated with 200 ml ether. The product was filtered off and air dried, giving 8.5 g N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6-methoxy-1-methylisoquinoline, m.p. 176°-178° (86%).