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【结 构 式】

【分子编号】44065

【品名】(1S)-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; (1S)-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether

【CA登记号】

【 分 子 式 】C18H21NO2

【 分 子 量 】283.37028

【元素组成】C 76.3% H 7.47% N 4.94% O 11.29%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

The optical resolution of the racemic 7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (I) (+)- or (-)-dibenzoyltartaric acid gives the corresponding (S)-isomer (II), which is N-demethylated by means of CN-Br to yield 7,8-dimethoxy-1(S)-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (III). Finally, this compound is fully demethylated by treatment with MsOH and methionine. An earlier alternative route to demethylation of (III) involves its conversion to the N-benzyl derivative (V) with benzyl bromide (IV), followed by demethylation with BBr3, yielding (VI), and final debenzylation with H2 over Pd/C.

1 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.
2 Bass, L.S.; Dandridge, P.A.; Setler, P.E.; Sarau, H.M.; Garvey, E.; Clardy, J.; Hanhn, R.A.; Kaiser, C.; Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine. J Med Chem 1982, 25, 6, 697-703.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 44063 7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether C19H23NO2 详情 详情
(II) 44064 (1S)-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether; (1S)-7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine C19H23NO2 详情 详情
(III) 44065 (1S)-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; (1S)-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether C18H21NO2 详情 详情
(IV) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(V) 44066 (1S)-3-benzyl-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether; (1S)-3-benzyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine C25H27NO2 详情 详情
(VI) 44067 (1S)-3-benzyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol C23H23NO2 详情 详情
Extended Information