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【结 构 式】

【分子编号】57250

【品名】4-(2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)-2-(hydroxymethyl)phenol

【CA登记号】

【 分 子 式 】C32H43NO4

【 分 子 量 】505.69776

【元素组成】C 76% H 8.57% N 2.77% O 12.66%

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:(VIII)

The condensation of 1,6-dibromohexane (I) with 4-phenyl-1-butanol (II) by means of NaOH under phase transfer catalysis gives 6-(4-phenylbutoxy)hexyl bromide (III), which is condensed with benzylamine (IV) by means of Cs2CO3 in hot DMF to yield the secondary amine (V). The condensation of (V) with methyl alpha-bromo 4-acetylsalicylate (VI) by means of DIEA in refluxing THF affords the tertiary amine (VII), which is submitted to a reductive deuteration by means of deuterated LiAlD4 in THF to provide the trideuterated intermediate (VIII). Finally this compound is deprotected by hydrogenation with H2 over Pd/C in methanol to give rise to the target trideuterated salmeterol.

1 Molinski, T.F.; Stanley, S.D.; Improved synthesis of 13C,2H3- and 2H3-salmeterol by Cs2CO3-mediated monoalkylation of a primary amine. J Label Compd Radiopharm 2002, 45, 9, 755.
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) 24786 1,6-dibromohexane 629-03-8 C6H12Br2 详情 详情
(II) 27291 4-phenyl-1-butanol 3360-41-6 C10H14O 详情 详情
(III) 31479 1-[4-[(6-bromohexyl)oxy]butyl]benzene; 6-bromohexyl-4-phenylbutyl ether; 6-Bromohexyloxybutylbenzene 94749-73-2 C16H25BrO 详情 详情
(IV) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(V) 35836 methyl 5-(2-bromoacetyl)-2-hydroxybenzoate C10H9BrO4 详情 详情
(VI) 35837 N-benzyl-6-(4-phenylbutoxy)-1-hexanamine; N-benzyl-N-[6-(4-phenylbutoxy)hexyl]amine C23H33NO 详情 详情
(VII) 35838 methyl 5-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]acetyl)-2-hydroxybenzoate C33H41NO5 详情 详情
(VIII) 35839 4-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]-1-hydroxyethyl)-2-(hydroxymethyl)phenol C32H43NO4 详情 详情
(VIII) 57250 4-(2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)-2-(hydroxymethyl)phenol C32H43NO4 详情 详情
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