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【结 构 式】 
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【分子编号】52358 【品名】(1R)-1-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[(1R)-2-hydroxy-1-phenylethyl][6-(4-phenylbutoxy)hexyl]amino}-1-ethanol 【CA登记号】 |
【 分 子 式 】C40H51NO5 【 分 子 量 】625.84868 【元素组成】C 76.77% H 8.21% N 2.24% O 12.78% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of 6-(4-phenylbutoxy)hexanol methanesulfonate (I) with (R)-phenylglycinol (II) by means of DIEA and NaI in hot acetonitrile gives the secondary amine (III), which is condensed with 2-(benzyloxy)-5-(2-bromoacetyl)benzoic acid methyl ester (IV) by means of DIEA in refluxing 1,2-dimethoxyethane to yield the tertiary amine (V). The enantioselective reduction of (V) with LiBH4 in refluxing dimethoxyethane affords the tetrahydroxy derivative (VI), which is finally debenzylated by hydrogenation with H2 over Pd/C in ethanol to provide the target aminoethanol derivative.
| 【1】 Evans, B. (GlaxoSmithKline plc); Phenethanolamine cpds.. AU 9163901; EP 0422889; JP 1991133946 . |
| 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) | 52354 | 6-[(4-phenylbutyl)oxy]hexyl methanesulfonate | C17H28O4S | 详情 | 详情 | |
| (II) | 14376 | (2R)-2-amino-2-phenyl-1-ethanol; (R)-(-)-2-phenylglycinol; (R)-2-amino-2-phenyl-1-ethanol | 56613-80-0 | C8H11NO | 详情 | 详情 |
| (III) | 52355 | 2-phenyl-2-({6-[(4-phenylbutyl)oxy]hexyl}amino)-1-ethanol | C24H35NO2 | 详情 | 详情 | |
| (IV) | 52356 | methyl 5-(2-bromoacetyl)-2-[(phenylmethyl)oxy]benzoate | C17H15BrO4 | 详情 | 详情 | |
| (V) | 52357 | methyl 5-[2-((2-hydroxy-1-phenylethyl){6-[(4-phenylbutyl)oxy]hexyl}amino)acetyl]-2-[(phenylmethyl)oxy]benzoate | C41H49NO6 | 详情 | 详情 | |
| (VI) | 52358 | (1R)-1-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[(1R)-2-hydroxy-1-phenylethyl][6-(4-phenylbutoxy)hexyl]amino}-1-ethanol | C40H51NO5 | 详情 | 详情 |